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Australian Journal of Chemistry Australian Journal of Chemistry Society
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Continuous Flow Synthesis of Difluoroamine Systems by Direct Fluorination

Christopher B. McPake A , Christopher B. Murray B C and Graham Sandford A C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK.

B AWE, Aldermaston, Reading, Berkshire, RG7 4PR, UK.

C Corresponding authors. Email: christopher.murray@awe.co.uk; graham.sandford@durham.ac.uk

Australian Journal of Chemistry 66(2) 145-150 https://doi.org/10.1071/CH12381
Submitted: 15 August 2012  Accepted: 27 September 2012   Published: 17 January 2013

Abstract

Continuous flow methodology for the synthesis of perfluoroaryl difluoroamine derivatives by reaction of fluorine gas with an appropriate perfluoroaniline substrate is described, further demonstrating the efficient use of flow regimes for reactions involving highly reactive and toxic reagents.


References

[1]  W. Ehrfeld, V. Hessel, H. Lowe, Microreactors: New Technology for Modern Chemistry 2000 (Wiley-VCH: New York, NY).

[2]  C. Wiles, P. Watts, Micro Reactor Technology in Organic Synthesis 2011 (CRC Press: Boca Raton, FL).

[3]  F. E. Valera, M. Quaranta, A. Moran, J. Blacker, A. Armstrong, J. T. Cabral, D. G. Blackmond, Angew. Chem. Int. Ed. 2010, 49, 2478.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXktVajsLk%3D&md5=8168ea37d350e22d92ace093e84401e0CAS |

[4]  G. Sandford, J. Fluor. Chem. 2007, 128, 90.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXnvFKksw%3D%3D&md5=1e8c729427ae3acb74d26ee36737ffb0CAS |

[5]  R. D. Chambers, M. A. Fox, D. Holling, T. Nakano, T. Okazoe, G. Sandford, Lab Chip 2005, 5, 191.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXmsV2hug%3D%3D&md5=f99004e1c86df3ac4f51521c0bf0a8a3CAS |

[6]  R. D. Chambers, D. Holling, G. Sandford, PCT/GB03/01993 2002.

[7]  R. D. Chambers, J. Hutchinson, M. E. Sparrowhawk, G. Sandford, J. S. Moilliet, J. Thomson, J. Fluor. Chem. 2000, 102, 169.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXitVSluro%3D&md5=47876c230b405a90f8ca9b2ade228212CAS |

[8]  R. D. Chambers, M. Parsons, G. Sandford, C. J. Skinner, M. J. Atherton, J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1 1999, 803.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXitVKksb0%3D&md5=8d03597d3d58b84eecffdd530bb13a86CAS |

[9]  D. Holling, G. Sandford, A. S. Batsanov, D. S. Yufit, J. A. K. Howard, J. Fluor. Chem. 2005, 126, 1377.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVymt7%2FP&md5=714d2064f1906a6aba1ce69e6095b62bCAS |

[10]  R. D. Chambers, M. P. Greenhall, J. Hutchinson, Tetrahedron 1996, 52, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXhtVSgurfM&md5=462f075a657620e6d2487f1accaf8327CAS |

[11]  R. D. Chambers, M. A. Fox, G. Sandford, Lab Chip 2005, 5, 1132.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVWmu7vP&md5=2efb9a86b2fac5235ce67bb9d9be3d72CAS |

[12]  K. Baum, J. Am. Chem. Soc. 1968, 90, 7083.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1MXhvFyntQ%3D%3D&md5=896e777d4290cb716ea86baf5c6afc98CAS |

[13]  R. K. Belter, J. Fluor. Chem. 2012, 137, 73.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xls1Whur0%3D&md5=866bd683370e6c85fbf55cf9e38343c5CAS |

[14]  R. D. Chapman, in High Energy Density Materials (Ed. T. M. Klapoetke) 2007, Vol. 125, pp. 123–151 (Springer: Berlin). 10.1007/430_2007_058

[15]  R. D. Chapman, M. C. Davis, R. Gilardi, Synth. Commun. 2003, 33, 4173.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpt12ht7Y%3D&md5=967510c5e5588569981c13321bffc6f3CAS |

[16]  R. D. Dresdner, F. N. Tlumac, J. A. Young, J. Am. Chem. Soc. 1960, 82, 5831.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3MXpvV2htA%3D%3D&md5=272a2522a47532b510afed77a0ab579bCAS |

[17]  W. P. Graham, J. P. Freeman, J. Am. Chem. Soc. 1967, 89, 716.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2sXosFertQ%3D%3D&md5=ef34d3f60d8b95a8c6b24ec749aa41fcCAS |

[18]  R. Haiges, R. D. Chapman, K. O. Christe, R. Wagner, J. A. Boatz, M. Yousufuddin, M. Etzkorn, G. K. S. Prakash, M. F. Welker, C. B. Kreutzberger, Angew. Chem. Int. Ed. 2006, 45, 5179.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xot12msL8%3D&md5=1aeedbbfcd2b7336fd04ff6a9948cc4fCAS |

[19]  G. K. S. Prakash, G. A. Olah, C. Bae, M. Kroll, J. Fluor. Chem. 2002, 117, 103.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  S. F. Reed, R. D. Shoults, J. Org. Chem. 1972, 37, 3326.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38Xls1eqtrw%3D&md5=37508bd09f472c1cacd25ceeb2c0ccafCAS |

[21]  C. M. Sharts, J. Org. Chem. 1968, 33, 1008.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXnslKhuw%3D%3D&md5=9715206eb572188812da313c0f0ccb5cCAS |

[22]  J. M. Shreeve, R. P. Singh, Chem. Commun. 2001, 1196.

[23]  A. V. Fokin, Y. N. Studnev, A. I. Rapkin, L. D. Kuznetsova, Russ. Chem. Bull. 1996, 45, 2547.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  T. Takagi, M. Tamura, M. Shibakami, H. Quan, A. Sekiya, J. Fluor. Chem. 2000, 101, 15.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXkslKhsw%3D%3D&md5=a48fe4430ebece37ed07d7ba9323862bCAS |

[25]  G. K. S. Prakash, G. A. Olah, M. Etzkorn, K. O. Christe, S. Schneider, A. Vij, Chem. Commun. 2002, 1712.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XlsFOlsLk%3D&md5=b3017256e1644da82adb8dd1e6648669CAS |

[26]  C. L. Coon, M. E. Hill, D. L. Ross, J. Org. Chem. 1968, 33, 1387.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXhtVClt74%3D&md5=1210473b40d2ea6dbeabb62fd5b468f2CAS |

[27]  M. W. Lerom, H. M. Peters, D. L. Ross, M. E. Hill, J. Dick, J. Chem. Eng. Data 1974, 19, 389.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXltVCrurg%3D&md5=99a44cb2c11f5531a690409749a5b699CAS |

[28]  R. K. Belter, J. Fluor. Chem. 2011, 132, 961.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFKhsrfK&md5=7fe79f9c7c802ca88e19b295d46ce072CAS |

[29]  C. A. Hargreaves, G. Sandford, R. Slater, D. S. Yufit, J. A. K. Howard, A. Vong, Tetrahedron 2007, 63, 5204.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXlt1Gqurs%3D&md5=f4250644955fa0bf5eb351a4d34d8060CAS |

[30]  G. Sandford, R. Slater, D. S. Yufit, J. A. K. Howard, A. Vong, J. Org. Chem. 2005, 70, 7208.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXnt1Sit7Y%3D&md5=4aef33d6827b1d53946c41580a104e80CAS |

[31]  R. D. Chambers, Fluorine in Organic Chemistry 2004 (Blackwell: Oxford).

[32]  W. R. Dolbier, Guide to Fluorine NMR for Organic Chemists 2009 (John Wiley and Sons: New York, NY).

[33]  R. D. Chambers, P. A. Martin, G. Sandford, D. L. H. Williams, J. Fluor. Chem. 2008, 129, 998.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtF2ktbbO&md5=5875672d45738cd737f2de3809f78c2aCAS |

[34]  R. D. Chambers, P. A. Martin, J. S. Waterhouse, D. L. H. Williams, B. Anderson, J. Fluor. Chem. 1982, 20, 507.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XkvFWgsrk%3D&md5=d3007895c7849d85e5f194f5c322aeb2CAS |

[35]  G. M. Brooke, J. Chem. Soc. 1961, 802.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3MXoslaqtA%3D%3D&md5=5d24ee79e4e552ce87cc18ef5089b5b9CAS |

[36]  L. J. Belf, M. W. Buxton, J. F. Tilney-Bassett, Tetrahedron 1967, 23, 4719.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXis1Kj&md5=c4461e13de474776275b2fb6a461b226CAS |

[37]  R. D. Chambers, J. Hutchinson, G. Sandford, J. Fluor. Chem. 1999, 100, 63.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXnvFSls7o%3D&md5=abd80b931bafa3400d605875f1a6d345CAS |

[38]  R. J. Koshar, D. R. Husted, C. D. Wright, J. Org. Chem. 1967, 32, 3859.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXitFClsw%3D%3D&md5=ba1749cde24ce4e2f3ed3575fc28d70fCAS |

[39]  American Environmental Group Ltd, AEGL (Acute Exposure Guideline Level) (50) October 2 2009.