Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
REVIEW

Flash (Vacuum) Pyrolysis Apparatus and Methods*

Curt Wentrup
+ Author Affiliations
- Author Affiliations

School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia. Email: wentrup@uq.edu.au




Curt Wentrup was educated at the University of Copenhagen (Cand. Scient. 1966 with K. A. Jensen; D.Sc. 1976) and the Australian National University (Ph.D. 1969 with W. D. Crow). After post-doctoral periods with Hans Dahn (Lausanne), W. M. Jones (Gainesville, FL), and Maitland Jones, Jr (Princeton), he held an assistant professorship at the Université de Lausanne, Switzerland, and a professorship at the Universität Marburg, Germany, before returning to Australia in 1985 as Professor and chair of organic chemistry and head of the organic chemistry section at the University of Queensland, where he is now Emeritus Professor. He has been the editor-in-chief of the Australian Journal of Chemistry since 2008, and chair (now immediate-past chair) of the National Committee for Chemistry of the Australian Academy of Science, of which he is a Fellow, since 2009. He has published over 300 research papers as well as over 30 reviews, chapters, and books. His interests are in the fields of both experimental and computational chemistry of reactive intermediates and unusual molecules using photochemistry, flash vacuum thermolysis, and microwave-induced chemical reactions; in particular, chemistry of nitrenes, carbenes, cumulenes, nitrile ylides, and nitrile imines, pericyclic rearrangements of cyanates, isocyanates, thio- and isothiocyanates, and nitrile oxides and sulfides, and the chemistry of extended cumulenes. He is a recipient of the 2003 Centenary Medal of the Australian Commonwealth for research in organic and physical chemistry, and the 2014 David Craig Medal of the Australian Academy of Science, and he is a JSPS Fellow in 2014.

Australian Journal of Chemistry 67(9) 1150-1165 https://doi.org/10.1071/CH14096
Submitted: 25 February 2014  Accepted: 21 March 2014   Published: 30 April 2014

Abstract

The history of pyrolysis equipment, methods, and reactions is narrated in the Introduction. Detailed descriptions of flash vacuum pyrolysis (FVP) (or thermolysis, FVT) apparatus for preparative and spectroscopic (UV, IR, electron spin resonance) purposes with product isolation at 77 K or in Ar matrices at ~10 K are presented. Very low pressure pyrolysis (VLPP), laser pyrolysis, and pulsed pyrolysis (jet flash pyrolysis) are also described together with illustrations of apparatus. The solvent spray flash vacuum pyrolysis (SS-FVP) of liquids or solutions of compounds of low volatility is described together with methods for the addition of solids to a pyrolysis tube, in particular details of pipto-pyrolysis (‘falling solid pyrolysis’). Methods used for catalytic vacuum gas–solid reactions (VGSR) are also summarised.


References

[1]     (a) See, for example, Blaise de Vigenere Traicté du Feu et du Sel 1618 (Abel l’Angelier: Paris). Reprinted 1976 (Jobert: Paris).
         (b) Die Alchemie des Andreas Libavius, Ein Lehrbuch der Chemie aus dem Jahre 1597 1964 (Verlag Chemie: Weinhein).

[2]  H. Kolbe, Ann. Chim. Pharm. 1845, 54, 145.
         | CrossRef |

[3]  F. Wöhler, Ann. Chim. Phys. 1828, 37, 330.

[4]  W. G. Mixter, Am. Chem. J. 1882, 4, 35.

[5]  E. Mitscherlich, Justus Liebigs Ann. Chem. 1834, 9, 39.

[6]  (a) W. Heintz, Poggendorffs Ann. Phys. Chem. 1854, 93, 519.
         | CrossRef |
      (b) See also C. H. DePuy, R. W. King, Chem. Rev. 1960, 60, 431.
         | CrossRef |
         (c) A. Maccoll, in The Chemistry of Alkenes (Ed. S. Patai) 1964, pp. 203–240 (Wiley: New York, NY).
      (d) G. G. Smith, F. W. Kelly, Progr. Phys. Org. Chem. 1971, 8, 75.

[7]  M. Berthelot, Bull. Soc. Chim. 1867, 7, 274.

[8]  C. Graebe, Ber. Dtsch. Chem. Ges. 1872, 5, 376.
         | CrossRef |

[9]  C. Graebe, Justus Liebigs Ann. Chem. 1874, 174, 177.
         | CrossRef |

[10]  C. Graebe, F. Ullmann, Justus Liebigs Ann. Chem. 1896, 291, 16.
         | CrossRef | 1:CAS:528:DyaD28XovVyhsA%3D%3D&md5=0907d87ea9bb7dff15de67fed9b7cf18CAS |

[11]  P. Ferko, Ber. Dtsch. Chem. Ges. 1887, 20, 660.
         | CrossRef |

[12]  E. Frémy, Encyclopédie Chimique 1882 (Dunod: Paris), Vol. 1, Atlas Fig. 204; Bibliothèque Nationale de France, Paris. Available at http://www2.biusante.parisdescartes.fr/livanc/?p=30&cote=pharma_018935x03x1&do=page (accessed 19 February 2014).

[13]  (a) The design of the Bunsen burner was first published in 1857: R. Bunsen, H. E. Roscoe, Poggendorffs Ann. Chem. Phys. 1857, 100, 43.
         | CrossRef |
         (b) Gesammelte Abhandlungen von Robert Bunsen (Eds W. Ostwald, M. Bodenstein) 1904 (W. Engelmann: Leipzig).
      (c) W. B. Jensen, J. Chem. Educ. 2005, 82, 518.
         | CrossRef |

[14]  C. Graebe, Ber. Dtsch. Chem. Ges. 1884, 17, 1370.
         | CrossRef |

[15]  A. Pictet, H. J. Ankersmit, Justus Liebigs Ann. Chem. 1891, 266, 138.
         | CrossRef |

[16]  A. Claus, Ber Dtsch. Chem. Ges. 1875, 8, 37.
         | CrossRef |

[17]  (a) A. Mardyukov, W. Sander, Chem. – Eur. J. 2009, 15, 1462.
         | CrossRef | 1:CAS:528:DC%2BD1MXhslCqsbk%3D&md5=f78e2bce71c04534600d420e09acf4aaCAS | 19132699PubMed |
      (b) A. Mardyukov, W. Sander, Eur. J. Org. Chem. 2010, 2904.
         | CrossRef |

[18]  H. Meyer, A. Hofmann, Monatsh. Chem. 1916, 37, 681.
         | CrossRef | 1:CAS:528:DyaC2sXjvVym&md5=e1d12ff70b47873a93f46f3b166c3624CAS |

[19]  W. Löb, Ber. Dtsch. Chem. Ges. 1901, 34, 915.
         | CrossRef |

[20]  A. W. v. Hofmann, Ber. Dtsch. Chem. Ges. 1890, 23, 3303.
         | CrossRef |

[21]  C. D. Hurd, The Pyrolysis of Carbon Compounds 1929 (Chemical Catalog Company: New York, NY).

[22]  C. D. Hurd, F. H. Blunck, J. Am. Chem. Soc. 1938, 60, 2419.
         | CrossRef | 1:CAS:528:DyaA1MXpvFc%3D&md5=f7a42247980575684c20cb5fa98052c1CAS |

[23]  (a) C. D. Hurd, Org. Synth. 1925, 4, 39.
         | CrossRef |
      (b) C. D. Hurd, Org. Synth. Coll. Vol. 1 1941, 330.

[24]  J. W. Williams, C. D. Hurd, J. Org. Chem. 1940, 5, 122.
         | CrossRef | 1:CAS:528:DyaH3cXitFWqsg%3D%3D&md5=693d010237f764c50d2e7b38d35ec7a3CAS |

[25]  H. Bibas, M. W. Wong, C. Wentrup, Chem. – Eur. J. 1997, 3, 237.
         | CrossRef | 1:CAS:528:DyaK2sXhvVygsr8%3D&md5=253018aa43783c96c1d37ab59d36b507CAS | 24022954PubMed |

[26]  H. Sainte-Claire Deville, Compt. Rend. Séances Acad. Sci. (Paris) 1864, 59, 117.

[27]  H. Sainte-Claire Deville, Leçons sur la Dissociation Professées Devant la Société Chimique 1864 (Imprimérie Générale de Ch. Lahore: Paris); Bibliothèque Nationale de France. Available at http://gallica.bnf.fr/ark:/12148/bpt6k96098t (accessed 19 February 2014).

[28]  H. H. G. Jellinek, J. Chem. Educ. 1986, 63, 1029.
         | CrossRef | 1:CAS:528:DyaL2sXms1Cnsg%3D%3D&md5=dc2e05bf6ba451a8fb2e792b5225449bCAS |

[29]  G. M. Badger, R. M. Buttery, R. W. L. Kimber, G. E. Lewis, A. G. Moritz, I. M. Napier, J. Chem. Soc. 1958, 2449.and subsequent papers
         | CrossRef | 1:CAS:528:DyaG1cXhtFemurs%3D&md5=2b95e740faa1cdc7518cff20d99d7f63CAS |

[30]  R. F. C. Brown, Pyrolytic Methods in Organic Chemistry 1980 (Academic Press: New York, NY).

[31]  (a) F. Paneth, W. Hofeditz, Ber. Dtsch. Chem. Ges. 1929, 62, 1335.
         | CrossRef |
         (b) F. O. Rice, K. K. Rice, The Aliphatic Free Radicals 1935 (The Williams and Wilkins Co.: Baltimore, MD).

[32]  (a) G. C. Eltenton, J. Chem. Phys. 1942, 10, 403.
         | CrossRef | 1:CAS:528:DyaH38XivVOqtg%3D%3D&md5=9ea19be1853f53be3941332f277fb818CAS |
      (b) G. C. Eltenton, J. Chem. Phys. 1947, 15, 455.
         | CrossRef |

[33]  J. A. Hipple, D. P. Stevenson, Phys. Rev. 1943, 63, 121.
         | CrossRef |

[34]  A. J. B. Robinson, Proc. R. Soc. Lond. 1949, A199, 394.

[35]  (a) P. LeGoff, J. Chim. Phys. 1953, 50, 423.
         | 1:CAS:528:DyaG2cXhslektQ%3D%3D&md5=274cb957b4ee27e5dce724f1974d85a8CAS |
      (b) P. LeGoff, J. Chim. Phys. 1956, 53, 269.

[36]  (a) F. P. Lossing, A. W. Tickner, J. Chem. Phys. 1952, 20, 907.
         | CrossRef | 1:CAS:528:DyaG3sXhtFChtQ%3D%3D&md5=b5467fabaddcc2a712f744cd1b971913CAS |
      (b) K. U. Ingold, F. P. Lossing, J. Chem. Phys. 1953, 21, 1135.
         | CrossRef |
      (c) F. P. Lossing, K. U. Ingold, A. W. Tickner, Discuss. Faraday Soc. 1953, 14, 34.
         | CrossRef |
      (d) F. P. Lossing, P. Kebarle, J. B. DeSousa, Adv. Mass Spectrom. 1959, 1, 431.

[37]  L. D. Wescott, P. S. Skell, J. Am. Chem. Soc. 1965, 87, 1721.
         | CrossRef | 1:CAS:528:DyaF2MXot1Sqtg%3D%3D&md5=554d8f5e8fe710c6310ebb74d2c54af0CAS |

[38]  P. S. Skell, L. D. Westcott, J. P. Goldstein, R. R. Engel, J. Am. Chem. Soc. 1965, 87, 2829.
         | CrossRef | 1:CAS:528:DyaF2MXks1aitro%3D&md5=5e6cb9b7655d28b1c9ef04c8e78b5d70CAS |

[39]  F. P. Lossing, in Mass Spectrometry of Free Radicals (Ed. C. A. McDowell) 1963, Ch. 11, pp. 442–505 (McGraw-Hill: New York, NY).

[40]  (a) R. F. C. Brown, R. K. Solly, Chem. Ind. (London) 1965, 181.
         | 1:CAS:528:DyaF2MXktlOnuw%3D%3D&md5=e433f59e48c3e126e9f53009c6d8f002CAS |
      (b) R. F. C. Brown, W. D. Crow, R. K. Solly, Chem. Ind. (London) 1966, 343.
      (c) W. D. Crow, R. K. Solly, Aust. J. Chem. 1966, 19, 2119.
         | CrossRef |
      (d) R. F. C. Brown, D. V. Gardner, J. F. W. McOmie, R. K. Solly, Aust. J. Chem. 1967, 20, 139.
         | CrossRef |

[41]  (a) W. D. Crow, C. Wentrup, Tetrahedron Lett. 1967, 8, 4379.
         | CrossRef |
      (b) W. D. Crow, C. Wentrup, J. Chem. Soc., Chem. Commun. 1968, 1026.
         | CrossRef |
      (c) W. D. Crow, C. Wentrup, J. Chem. Soc., Chem. Commun. 1968, 1082.
         | CrossRef |
      (d) W. D. Crow, C. Wentrup, Tetrahedron Lett. 1968, 9, 5569.
         | CrossRef |
      (e) W. D. Crow, C. Wentrup, Tetrahedron Lett. 1968, 9, 6149.
         | CrossRef |
      (f) C. Wentrup, J. Chem. Soc., Chem. Commun. 1969, 1386.
         | CrossRef |
      (g) W. D. Crow, C. Wentrup, J. Chem. Soc., Chem. Commun. 1969, 1387.
         | CrossRef |

[42]  (a) R. F. C. Brown, F. W. Eastwood, Synlett 1993, 9.
         | CrossRef | 1:CAS:528:DyaK3sXhtVWmtL4%3D&md5=ed3ccc6e7e3de4cd1f3079e2bd839175CAS |
      (b) R. F. C. Brown, K. J. Harrington, G. L. McMullen, J. Chem. Soc., Chem. Commun. 1974, 123.
         | CrossRef |
      (c) R. F. C. Brown, F. W. Eastwood, K. J. Harrington, G. L. McMullen, Aust. J. Chem. 1974, 27, 2393.
      (d) R. F. C. Brown, F. W. Eastwood, G. P. Jackman, Aust. J. Chem. 1977, 30, 1757.
         | CrossRef |
      (e) R. F. C. Brown, F. W. Eastwood, G. P. Jackman, Aust. J. Chem. 1978, 31, 579.
         | CrossRef |

[43]  E. Hedaya, D. W. McNeil, J. Am. Chem. Soc. 1967, 89, 4213.
         | CrossRef | 1:CAS:528:DyaF2sXltVyjsb8%3D&md5=4de8e3dcf346db714968a43b213b41e7CAS |

[44]  E. Hedaya, Acc. Chem. Res. 1969, 2, 367.
         | CrossRef | 1:CAS:528:DyaE3cXms1Shuw%3D%3D&md5=a1ea7e0987574360bbe066e589a07511CAS |

[45]  (a) C. L. Angell, E. Hedaya, D. McLeod, J. Am. Chem. Soc. 1967, 89, 4214.
         | CrossRef | 1:CAS:528:DyaF2sXltVyjsbw%3D&md5=5d5f35a6b9ec70527856d9eeeec30583CAS |
      (b) P. Schissel, D. J. McAdoo, E. Hedaya, D. W. McNeil, J. Chem. Phys. 1968, 49, 5061.
         | CrossRef |
      (c) E. Hedaya, D. W. McNeil, P. Schissel, D. J. McAdoo, J. Am. Chem. Soc. 1968, 90, 5284.
         | CrossRef |

[46]  (a) W. Weltner, Science 1967, 155, 155.
         | CrossRef | 1:CAS:528:DyaF2sXntVegtw%3D%3D&md5=9d9601a8ccf7513f23651ab302fd6b60CAS | 17738213PubMed |
      (b) P. H. Kasai, E. B. Whipple, W. Weltner, J. Chem. Phys. 1966, 44, 2581.
         | CrossRef |

[47]  (a) C. Wentrup, D. Kvaskoff, Aust. J. Chem. 2013, 66, 286. (see the Supplementary Material)
         | CrossRef | 1:CAS:528:DC%2BC3sXksF2murk%3D&md5=2117085745291f10f9914a0a3795df41CAS |
      (b) M. Høj, D. Kvaskoff, C. Wentrup, J. Org. Chem. 2014, 79, 307.
         | CrossRef |
      (c) S. Torker, D. Kvaskoff, C. Wentrup, J. Org. Chem. 2014, 79, 1758.
         | CrossRef |
      (d) D. Kvaskoff, P. Bednarek, L. George, S. Pankarakshan, C. Wentrup, J. Org. Chem. 2005, 70, 7947.
         | CrossRef |
      (e) M. Kuzaj, H. Lüerssen, C. Wentrup, Angew. Chem. Int. Ed. 1986, 25, 480.
         | CrossRef |

[48]  (a) P. de Mayo, Endeavour 1972, 31, 135.
         | 1:CAS:528:DyaE38XlsFWjurY%3D&md5=647a784cb0cd69c0193043fa2e931e1cCAS |
      (b) J. F. King, P. de Mayo, C. L. McIntosh, K. Piers, D. J. H. Smith, Can. J. Chem. 1970, 48, 3704.
         | CrossRef |

[49]  J. F. King, R. A. Marty, P. de Mayo, D. L. Verdun, J. Am. Chem. Soc. 1971, 93, 6304.
         | CrossRef | 1:CAS:528:DyaE38XhtlGksA%3D%3D&md5=2f411171dbee8c38cf9e463d5ab53c38CAS |

[50]  G. Seybold, Angew. Chem. Int. Ed. 1977, 16, 365.
         | CrossRef |

[51]  G. Seybold, G. Heibl, Chem. Ber. 1977, 110, 1225.
         | CrossRef | 1:CAS:528:DyaE2sXkt1alur0%3D&md5=a8f04fda69e3d25a59c180f2d1897010CAS |

[52]  U. E. Wiersum, Aldrichim Acta 1981, 14, 53.
         | 1:CAS:528:DyaL3MXmtF2qs7g%3D&md5=0beff484d9cc80ca50c03216d60869b7CAS |

[53]  U. E. Wiersum, Aldrichim Acta 1984, 17, 31.
         | 1:CAS:528:DyaL2cXlsFWjsr8%3D&md5=25d33d7d11b879d9c0cc91706025c261CAS |

[54]  (a) U. E. Wiersum, Recl. Trav. Chim. Pays Bas 1982, 101, 317.
         | CrossRef | 1:CAS:528:DyaL3sXjtlyktQ%3D%3D&md5=1cd1c05049368a81471211b317f31af9CAS |
      (b) U. E. Wiersum, Recl. Trav. Chim. Pays Bas 1982, 101, 365.
         | CrossRef |

[55]  (a) W. S. Trahanovsky, J. L. Tunkel, J. C. Thoen, Y. Wang, J. Org. Chem. 1995, 60, 8407.
         | CrossRef | 1:CAS:528:DyaK2MXpvVaqsbc%3D&md5=10ba3f9899063aec3770c5f96dd30932CAS |
      (b) W. S. Trahanovsky, S.-K. Lee, J. W. Fennell, J. Org. Chem. 1995, 60, 8410.
         | CrossRef |

[56]  R. A. Frey, R. D. Werder, H. H. Günthard, J. Mol. Spectrosc. 1970, 35, 260.
         | CrossRef | 1:CAS:528:DyaE3cXks1Srs7w%3D&md5=abe9b06604d6e497ae8a12d0a7bbed0dCAS |

[57]  M. Knudsen, Ann. Phys. 1909, 28, 75.999.
         | 1:CAS:528:DyaD1MXpvV2r&md5=3eccb55194792b7ae9c5794973f3e36eCAS |

[58]  J. M. Pearson, H. A. Six, D. J. Williams, M. Levy, J. Am. Chem. Soc. 1971, 93, 5034.
         | CrossRef | 1:CAS:528:DyaE3MXlt1yqu7g%3D&md5=e575ca15e8d02ac3bd823079371230b3CAS |

[59]     (a) W. F. Gorham, “Para-Xylylene Polymers (by the Pyrolysis of Di-para-xylylene)”, U.S. Patent 3 342 754A 670919 1967 (Union Carbide).
      (b) W. F. Gorham, J. Polym. Sci., Part A-1 1966, 4, 3027.
         | CrossRef |

[60]  G. Schaden, J. Anal. Appl. Pyr. 1979, 1, 159.
         | CrossRef | 1:CAS:528:DyaL3cXnsFGrtw%3D%3D&md5=0a74177cceddae4d9f3933c003739c5fCAS |

[61]  G. Maier, G. Miehm, H. P. Reisenauer, Chem. Ber. 1982, 115, 801.
         | CrossRef | 1:CAS:528:DyaL38XhsVaqtrs%3D&md5=8f0f359dc5d936a73a8f5761e13e8f62CAS |

[62]  H. Egsgaard, L. Carlsen, J. Anal. Appl. Pyr. 1983, 5, 1.
         | CrossRef | 1:CAS:528:DyaL3sXktlOrur4%3D&md5=8846443ee525e63fd48a057da61eb458CAS |

[63]  C. Wentrup, R. Blanch, H. Briehl, G. Gross, J. Am. Chem. Soc. 1988, 110, 1874.
         | CrossRef | 1:CAS:528:DyaL1cXhtlWmtro%3D&md5=8ea4586336a3f00847912cff539a522cCAS |

[64]  C. Wentrup, P. Lorencak, J. Am. Chem. Soc. 1988, 110, 1880.
         | CrossRef | 1:CAS:528:DyaL1cXhtlSquro%3D&md5=e98ed63e19f029d6414c0818b3feb707CAS |

[65]  C. Wentrup, Acta Chem. Scand. 1966, 20, 2128.
         | CrossRef | 1:CAS:528:DyaF2sXktVaksr0%3D&md5=83a92d2383bda5095262d7a0b9e77060CAS |

[66]  (a) RNC3O: T. Mosandl, C. O. Kappe, R. Flammang, C. Wentrup, J. Chem. Soc., Chem. Commun. 1992, 1571.
         | CrossRef | 1:CAS:528:DyaK3sXlvFeluw%3D%3D&md5=4a3a5a84214672903c5aeff7c62f2de6CAS |
      (b) R. Flammang, S. Laurent, M. Flammang-Barbieux, C. Wentrup, Rapid Commun. Mass Spectrom. 1992, 6, 667.
         | CrossRef |
      (c) C2S2: C. Wentrup, P. Kambouris, R. A. Evans, D. Owen, G. Macfarlane, J. Chuche, J. C. Pommelet, A. Ben Cheikh, M. Plisnier, R. Flammang, J. Am. Chem. Soc. 1991, 113, 3130.
         | CrossRef |
      (d) N2S: C. Wentrup, S. Fischer, A. Maquestiau, R. Flammang, J. Org. Chem. 1986, 51, 1908.
         | CrossRef |
      (e) P. Kambouris, T.-K. Ha, C. Wentrup, J. Phys. Chem. 1992, 96, 2065.
         | CrossRef |
      (f) H-C≡C-NH2, Ph-C≡C-NH2: C. Wentrup, H. Briehl, P. Lorencak, U. J. Vogelbacher, H.-W. Winter, A. Maquestiau, R. Flammang, J. Am. Chem. Soc. 1988, 110, 1337.
         | CrossRef |
      (g) Benzocyclobutenedione bisketene isomer: T. Mosandl, C. Wentrup, J. Org. Chem. 1993, 58, 747.
         | CrossRef |
      (h) Benzyne: T. Mosandl, G. Macfarlane, R. Flammang, C. Wentrup, Aust. J. Chem. 2010, 63, 1076.
         | CrossRef |
      (i) Nitrile imines: C. Wentrup, S. Fischer, A. Maquestiau, R. Flammang, Angew. Chem. Int. Ed. 1985, 24, 56.
         | CrossRef |
      (j) HCN dimers, C2H2N2: C. Wentrup, P. Lorencak, A. Maquestiau, R. Flammang, Chem. Phys. Lett. 1987, 137, 241.
         | CrossRef |

[67]  (a) J. Brown, R. Flammang, Y. Govaert, M. Plisnier, C. Wentrup, Y. Van Haverbeke, Rapid Commun. Mass Spectrom. 1992, 6, 249.
         | CrossRef | 1:CAS:528:DyaK38XitlCqtro%3D&md5=bc2b350c62bc4fce5171e4e5f8a1fd99CAS |
      (b) Review: C. Wentrup, R. Flammang, J. Phys. Org. Chem. 1998, 11, 350.
         | CrossRef |
      (c) Review: P. Gerbaux, L. Lamote, Y. Van Haverbeke, R. Flammang, J. M. Brown, Eur. J. Mass Spectrom. (Chichester, Eng.) 2012, 18, 93.
         | CrossRef |

[68]  H.-F. Grützmacher, J. Lohmann, Justus Liebigs Ann. Chem. 1967, 705, 81.
         | CrossRef |

[69]  L. Carlsen, H. Egsgaard, Thermochim. Acta 1980, 38, 47.
         | CrossRef | 1:CAS:528:DyaL3cXltlWrt7g%3D&md5=c031e6b173529bd76387e1a7b9018822CAS |

[70]  F. Turecek, Adv. Mass Spectrom. 1989, 11B, 1079.
         | 1:CAS:528:DyaK3cXhvVyjsLk%3D&md5=37d92d5d344f2343f0ed7c9e92c202b3CAS |

[71]  C. Wentrup, Aust. J. Chem. 2013, 66, 852.
         | CrossRef | 1:CAS:528:DC%2BC3sXht1Ois7%2FF&md5=f54aae903c10e96e32e154fc80719227CAS |

[72]  (a) S. W. Benson, G. N. Spokes, J. Am. Chem. Soc. 1967, 89, 2525.
         | CrossRef | 1:CAS:528:DyaF2sXkt1Kju7k%3D&md5=8796586f3448338434e60a1779a8efdfCAS |
      (b) D. M. Golden, G. N. Spokes, S. W. Benson, Angew. Chem. Int. Ed. 1973, 12, 534.
         | CrossRef |

[73]  N. H. Werstiuk, C. D. Roy, J. Ma, Can. J. Chem. 1994, 72, 2537.
         | CrossRef | 1:CAS:528:DyaK2MXisVyht74%3D&md5=c30fb3a9b258f7a5f678f25cf722c7a0CAS |

[74]  N. H. Werstiuk, C. D. Roy, J. Ma, Can. J. Chem. 1995, 73, 146.
         | CrossRef | 1:CAS:528:DyaK2MXksVSnuro%3D&md5=f862cc5e91b667fae8bd68adb5132687CAS |

[75]  (a) H. M. Muchall, N. H. Werstiuk, B. Choudhury, J. Warkentin, J. Pezacki, Can. J. Chem. 1998, 76, 238.
         | 1:CAS:528:DyaK1cXjt1amsLo%3D&md5=81fa9eb71a9fd2337f670835daf686a3CAS |
      (b) N. H. Werstiuk, A. Klys, J. Warkentin, Can. J. Chem. 2006, 84, 546.
         | CrossRef |

[76]  A. Chrostowska, G. Pfister-Guillouzo, F. Gracian, C. Wentrup, Aust. J. Chem. 2010, 63, 1084.
         | CrossRef | 1:CAS:528:DC%2BC3cXosl2hsLY%3D&md5=e5e18272fc13509b1dcdefdc69ac342fCAS |

[77]  C. Wentrup, R. Blanch, H. Briehl, G. Gross, J. Am. Chem. Soc. 1988, 110, 1874.
         | CrossRef | 1:CAS:528:DyaL1cXhtlWmtro%3D&md5=8ea4586336a3f00847912cff539a522cCAS |

[78]  (a) H. P. Reisenauer, J. Romanski, G. Mloston, P. R. Schreiner, Eur. J. Org. Chem. 2006, 4813.
         | CrossRef | 1:CAS:528:DC%2BD28Xht1aisbrK&md5=2836d697b2d965aec117c1146e46b5f7CAS |
      (b) P. R. Schreiner, H. P. Reisenauer, J. Romanski, G. Mloston, Angew. Chem. Int. Ed. 2006, 45, 3989.
         | CrossRef |

[79]  M. R. Berman, P. B. Comita, C. B. Moore, R. G. Bergman, J. Am. Chem. Soc. 1980, 102, 5692.
         | CrossRef | 1:CAS:528:DyaL3cXltlWrtb4%3D&md5=0bd551278f200239fbc09ef3f7f0787eCAS |

[80]  (a) J. E. Taylor, D. A. Hutchings, K. J. Frech, J. Am. Chem. Soc. 1969, 91, 2215.
         | CrossRef | 1:CAS:528:DyaF1MXkt1WmsrY%3D&md5=b8c590f3101815bd4fd75a10d7f055bbCAS |
      (b) G. Pratt, D. Rogers, J. Chem. Soc., Faraday Trans. I 1979, 75, 1089.
         | CrossRef |

[81]  (a) K. E. Lewis, D. F. McMillen, D. M. Golden, J. Phys. Chem. 1980, 84, 226.
         | CrossRef | 1:CAS:528:DyaL3cXnsFGrug%3D%3D&md5=9546d9bd1518e0c0fc1cd43e08851b32CAS |
      (b) D. F. McMillen, K. E. Lewis, G. P. Smith, D. M. Golden, J. Phys. Chem. 1982, 86, 709.
         | CrossRef |

[82]  L. T. Scott, M. A. Kirms, B. L. Earl, J. Chem. Soc., Chem. Commun. 1983, 1373.
         | CrossRef | 1:CAS:528:DyaL2cXhtVarsr4%3D&md5=4cb9f8d2d5d2a53aa461296dd10bc3c3CAS |

[83]  (a) L. T. Scott, J. Org. Chem. 1984, 49, 3021.
         | CrossRef | 1:CAS:528:DyaL2cXkslWqurg%3D&md5=107d4da9fce13d1a80850cdb9482c812CAS |
      (b) L. T. Scott, Acc. Chem. Res. 1982, 15, 52.
         | CrossRef |
      (c) R. W. Alder, S. P. East, J. N. Harvey, M. T. Oakley, J. Am. Chem. Soc. 2003, 125, 5375.
         | CrossRef |

[84]  J. Becker, C. Wentrup, E. Katz, K.-P. Zeller, J. Am. Chem. Soc. 1980, 102, 5110.
         | CrossRef | 1:CAS:528:DyaL3cXkvFCmtb0%3D&md5=696497d8dfd7bd59743ae50fba8f0963CAS |

[85]  G. R. Unruh, D. M. Birney, J. Am. Chem. Soc. 2003, 125, 8529.
         | CrossRef | 1:CAS:528:DC%2BD3sXkslensLs%3D&md5=50f7c183c9ad6d27f5d2d38ee026bccdCAS | 12848559PubMed |

[86]  O. Meth-Cohn, Acc. Chem. Res. 1987, 20, 18.
         | CrossRef | 1:CAS:528:DyaL2sXms1Krug%3D%3D&md5=aad2456c13f058ede26bfd23bdf0413eCAS |

[87]  Y. Rubin, S. S. Lin, C. B. Knobler, J. Anthony, A. M. Boldi, F. Diederich, J. Am. Chem. Soc. 1991, 113, 6943.
         | CrossRef | 1:CAS:528:DyaK3MXltFequr4%3D&md5=ca69f05975cb6b4c127334a85898ca7fCAS |

[88]  M. Regimbald-Krnel, C. Wentrup, J. Org. Chem. 1998, 63, 8417.
         | CrossRef | 1:CAS:528:DyaK1cXms12ju74%3D&md5=20b0c23e971ff6f2a610afbc0cc231edCAS |

[89]  J. Magrath, F. W. Fowler, Tetrahedron Lett. 1988, 29, 2171.
         | CrossRef | 1:CAS:528:DyaL1MXit12jsg%3D%3D&md5=f7fab3ec87d7efb2db34a0f25a3cd962CAS |

[90]  J. E. Everett, N. D. Renner, D. K. Russell, J. Chem. Soc, Chem. Commun. 1998, 341.
         | CrossRef | 1:CAS:528:DyaK1cXhtlKgsr4%3D&md5=80e89b0b452c8a4aaccf9c30fdb94d77CAS |

[91]  H. Dürr, H. Nickels, L. A. Pacala, M. Jones, J. Org. Chem. 1980, 45, 973.
         | CrossRef |

[92]  F. Vögtle, P. Fornell, W. Löhr, Chem. Ind. 1979, 416S.

[93]  (a) F. Vögtle, L. Rossa, Angew. Chem. 1979, 91, 534.
         | CrossRef |
      (b) X. Laufenberg, N. Feuerbacher, I. Pischel, O. Börsch, M. Nieger, F. Vögtle, Liebigs Ann. Chem.-Recueil 1997, 1901.
         | CrossRef |

[94]  (a) P. Schiess, S. Rutschmann, Chimia 1985, 39, 213.
         | 1:CAS:528:DyaL2MXlvFGrtL8%3D&md5=0cb73374b1a25eaf0216cfebfd4ecea7CAS |
      (b) P. Schiess, M. Heitzmann, S. Rutschmann, R. Stälheli, Tetrahedron Lett. 1978, 19, 4569.
         | CrossRef |

[95]  Y. Sekine, M. Brown, V. Boekelheide, J. Am. Chem. Soc. 1979, 101, 3126.
         | CrossRef | 1:CAS:528:DyaE1MXktlyqu74%3D&md5=645716afe532e80aaa9e28d9c1a3cf77CAS |

[96]  C. Wentrup, C. Major, J. Becker, H. J. Lindner, Tetrahedron 1985, 41, 1601.
         | CrossRef | 1:CAS:528:DyaL2MXlsVWjtb8%3D&md5=3f28094ab321cfd79321ab6e45795ee3CAS |

[97]  C. Wentrup, H.-W. Winter, Angew. Chem. Int. Ed. 1978, 17, 609.
         | CrossRef |

[98]  (a) H. Clauberg, D. W. Minsek, P. Chen, J. Am. Chem. Soc. 1992, 114, 99.
         | CrossRef | 1:CAS:528:DyaK38XktVOltA%3D%3D&md5=4f55f149b2999c34f9e0bd9dea566994CAS |
      (b) D. W. Kohn, H. Clauberg, P. Chen, Rev. Sci. Instrum. 1992, 63, 4003.
         | CrossRef |

[99]  (a) A. V. Friderichsen, J. G. Radziszewski, M. R. Nimlos, P. R. Winter, D. C. Dayton, D. E. David, G. B. Ellison, J. Am. Chem. Soc. 2001, 123, 1977.
         | CrossRef | 1:CAS:528:DC%2BD3MXos1Kjug%3D%3D&md5=d872e3a765a2511417ab9e91e359d176CAS | 11456819PubMed |
      (b) X. Zhang, A. V. Friderichsen, S. Nandi, G. B. Ellison, D. E. David, J. T. McKinnon, T. G. Lindeman, D. C. Dayton, M. R. Nimlos, Rev. Sci. Instrum. 2003, 74, 3077.
         | CrossRef |

[100]  (a) P. Chen, S. D. Colson, W. A. Chupka, J. A. Berson, J. Phys. Chem. 1986, 90, 2319.
         | CrossRef | 1:CAS:528:DyaL28XitFGksbg%3D&md5=273d9310775b061a31ce19ba1f927e8bCAS |
      (b) J. R. Dunlop, J. Karolczak, D. J. Clouthier, Chem. Phys. Lett. 1988, 151, 362.
         | CrossRef |
      (c) Z. Liu, R. J. Livingstone, P. B. Davies, Chem. Phys. Lett. 1998, 291, 480.
         | CrossRef |

[101]  A. C. Legon, Chem. Commun. 1996, 109.
         | CrossRef | 1:CAS:528:DyaK28XhsFChs78%3D&md5=9b06fffdb13405169bd4cd48b0abbebbCAS |

[102]  G. Maier, T. Preiss, H. P. Reisenauer, Chem. Ber. 1994, 127, 779.
         | CrossRef | 1:CAS:528:DyaK2cXkvVahsbw%3D&md5=80cff6963417ce6c62b0371cfd92cc4bCAS |

[103]  G. Maier, H. P. Reisenauer, H. Pacl, Angew. Chem. Int. Ed. 1994, 33, 1248.
         | CrossRef |

[104]  C. M. Nunes, I. Reva, T. M. V. D. Pinhoe e Melo, R. Fausto, T. Solomek, T. Bally, J. Am. Chem. Soc. 2011, 133, 18911.
         | CrossRef | 1:CAS:528:DC%2BC3MXhtlOnsrzI&md5=c05ee622dee08f0a5d9779d3a3ee53d2CAS | 21954865PubMed |

[105]  G. G. Qiao, W. Meutermans, M. W. Wong, M. Träubel, C. Wentrup, J. Am. Chem. Soc. 1996, 118, 3852.
         | CrossRef | 1:CAS:528:DyaK28XitVejurY%3D&md5=a8d2e4d9b1e1359a464568f63bc9cc79CAS |

[106]  C. T. Pedersen, F. Jensen, R. Flammang, Aust. J. Chem. 2009, 62, 69.
         | CrossRef | 1:CAS:528:DC%2BD1MXpvVWrtg%3D%3D&md5=b548c69ded69fdbddee067f56e1b05efCAS |

[107]  C. Wentrup, H. Bibas, A. Kuhn, U. Mitschke, M. C. McMills, J. Org. Chem. 2013, 78, 10705.
         | CrossRef | 1:CAS:528:DC%2BC3sXhsFyksb%2FF&md5=08beef9c335772d13c953088a2354454CAS | 24102481PubMed |

[108]  Descriptions with apparatus designs of numerous experiments of this kind can be found in Liebigs Experimentalvorlesung, Vorlesungsbuch und Kekulés Mitschrift 1983 (edited with commentary by O. P. Krätz and C. Priesner in collaboration with O. Kratz, A. Diem, and S. von Moisy) (Verlang Chemie: Weinheim).

[109]  C. Hansch, Chem. Rev. 1953, 53, 353.
         | CrossRef | 1:CAS:528:DyaG2cXhsVCntw%3D%3D&md5=b85a0abaf5b2c39268f2e84111d479abCAS |

[110]  N. D. Zelinsky, I. Titz, M. Gaverdowskaja, Ber. Dtsch. Chem. Ges 1926, 59, 2590.
         | CrossRef |

[111]  E. A. Dorko, J. Am. Chem. Soc. 1965, 87, 5518.
         | CrossRef | 1:CAS:528:DyaF28XjsFCgtg%3D%3D&md5=96f655db66c6826864ba6c67c3d2b4e8CAS |

[112]  A. E. Ginsberg, R. Paatz, F. Korte, Tetrahedron Lett. 1962, 3, 779.
         | CrossRef |

[113]  U. E. Wiersum, L. W. Jenneskens, Recl. Trav. Chim. Pays Bas 1991, 110, 129.
         | CrossRef | 1:CAS:528:DyaK3MXksVyktb8%3D&md5=f3f905cdb49328d45a832fcb22d7ee0cCAS |

[114]  U. E. Wiersum, L. W. Jenneskens, in Gas Phase Reactions in Organic Synthesis (Ed. Y. Vallée) 1997, Ch. 3, pp. 143–194 (Gordon and Breach: Amsterdam).

[115]  O. L. Chapman, C. C. Chang, R. N. Rosenquist, J. Am. Chem. Soc. 1976, 98, 261.
         | CrossRef | 1:CAS:528:DyaE28Xntl2mtw%3D%3D&md5=25da54ade553dcb5a8be72a71b3f7805CAS |

[116]  R. A. Aitken, P. K. G. Hodgson, A. O. Oyewale, J. J. Morrison, Chem. Commun. 1997, 1163.
         | CrossRef | 1:CAS:528:DyaK2sXkslShsLs%3D&md5=4e66827f400c267d7c7c802624b19fa0CAS |

[117]  J.-M. Denis, A.-C. Gaumont, in Gas Phase Reactions in Organic Synthesis (Ed. Y. Vallée) 1997, Ch. 4, pp. 195–238 (Gordon and Breach: Amsterdam).

[118]  J.-C. Guillemin, J.-M. Denis, M.-C. Lasne, J.-L. Ripoll, Tetrahedron 1988, 44, 4447.
         | CrossRef | 1:CAS:528:DyaL1MXpsVyktw%3D%3D&md5=bf62f11586e5ff022713c051c9b10cf9CAS |

[119]  (a) W. E. Billups, L.-J. Lin, E. W. Casserly, J. Am. Chem. Soc. 1984, 106, 3698.
         | CrossRef | 1:CAS:528:DyaL2cXktVKlt70%3D&md5=21d2aa659d6727ca98a963c6ca9a5072CAS |
      (b) W. E. Billups, L.-J. Lin, Tetrahedron 1986, 42, 1575.
         | CrossRef |

[120]  S. W. Staley, T. D. Norden, J. Am. Chem. Soc. 1984, 106, 3699.
         | CrossRef | 1:CAS:528:DyaL2cXktVKlt7s%3D&md5=ad9bb7f1dfe591aa045ede91e8bdda62CAS |

[121]  W. E. Billups, C.-A. Lee, B. E. Arney, K. H. Whitmire, J. Am. Chem. Soc. 1991, 113, 7980.
         | CrossRef | 1:CAS:528:DyaK3MXmtVOmtL4%3D&md5=bf7017c31a01e0447f01992972b5f1e3CAS |

[122]  U. H. Brinker, J. Ritzer, J. Am. Chem. Soc. 1981, 103, 2116.
         | CrossRef | 1:CAS:528:DyaL3MXhvFWgtb0%3D&md5=a9a8198f638459244b34c1159253a204CAS |

[123]  G. Kaup, D. Matthies, Mol. Cryst. Liq. Cryst. 1988, 161, 119.

[124]     (a) Pyrolysis: Theory and Industrial Practice (Eds L. F. Albright, B. L. Crynes, W. H. Corcoran) 1983 (Academic Press: New York, NY).
         (b) W. S. Donahue, J. C. Brandt, Pyrolysis: Types, Processes and Industrial Sources and Product 2009 (Nova Science Publishers: Hauppauge, NY).

[125]     (a) S. C. Moldoveanu, Pyrolysis of Organic Molecules: Applications to Health and Environmental Issues 2010 (Elsevier: Amsterdam).
         (b) T. P. Wampler, Applied Pyrolysis Handbook 2006 (CRC Press: Boca Raton, FL).
         (c) C. E. R. Jones, Analytical Pyrolysis 2012 (Elsevier: Amsterdam).

[126]  https://www.google.com.au/search?q=Pyrolysis+apparatus&tbm=isch&tbo=u&source=univ&sa=X&ei=lmb_UpiGGYTXkAXs7YH4CQ&ved=0CDgQsAQ&biw=1660&bih=885 (accessed 14 February 2014).

[127]     (a) S. C. Moldoveanu, Analytical Pyrolysis of Natural Organic Polymers 1998 (Elsevier: Amsterdam).
         (b) S. C. Moldoveanu, Analytical Pyrolysis of Synthetic Organic Polymers 2005 (Elsevier: Amsterdam).
         (c) http://www.frontier-lab.com/support/manual/PY-2020iD_E_Shimadzu (accessed 14 February 2014).

[128]  (a) H. Y. Cho, A. Ajaz, D. Himali, P. A. Waske, R. P. Johnson, J. Org. Chem. 2009, 74, 4137.
         | 1:CAS:528:DC%2BD1MXlsF2htLw%3D&md5=69b26a1fec94a554d56bba2da5d2a0d7CAS | 19432412PubMed |
      (b) K. J. Cahill, A. Ajaz, R. P. Johnson, Aust. J. Chem. 2009, 63, 1007.
      (c) A. Ajaz, A. C. Voukides, K. J. Cahill, R. Thamatam, S. L. Skraba-Joiner, R. P. Johnson, Aust. J. Chem. 2014, 67, 1301.
         | CrossRef |

[129]  (a) A. Laporterie, J. Marquie, J. Dubac, Microwaves Org. Synth. 2002, 219.
         | 1:CAS:528:DC%2BD3sXotFyqu7s%3D&md5=3e5a13f09a2ff386145e625de1fca79eCAS |
      (b) T. Besson, V. Thiery, J. Dubac, Microwaves Org. Synth. 2006, 1, 416.
      (c) J. Marquie, A. Laporterie, J. Dubac, N. Roques, Synlett 2001, 493.
      (d) B. Garrigues, R. Laurent, C. Laporte, A. Laporterie, J. Dubac, Liebigs Ann. Chem. 1996, 743.

[130]  D. Lecoq, B. A. Chalmers, R. N. Veedu, D. Kvaskoff, P. V. Bernhardt, C. Wentrup, Aust. J. Chem. 2009, 62, 1631.
         | 1:CAS:528:DC%2BD1MXhsFentrfP&md5=3e75528daf6047c6157c9c84b058b0c4CAS |

[131]  D. Cantillo, H. Sheibani, C. O. Kappe, J. Org. Chem. 2012, 77, 2463.
         | 1:CAS:528:DC%2BC38XitVeqs7k%3D&md5=117eeaa7f5b505a7565c5cfc31c8460aCAS | 22321044PubMed |

[132]  T. Razzaq, T. N. Glasnov, C. O. Kappe, Chem. Eng. Technol. 2009, 32, 1702.
         | 1:CAS:528:DC%2BD1MXhtlCrsLzI&md5=e695fb65e2a546cd090863a3897c3be0CAS |



Rent Article (via Deepdyve) Supplementary MaterialSupplementary Material (441 KB) Export Citation Cited By (3)

View Altmetrics