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Article << Previous     |     Next >>   Contents Vol 66(2)

Continuous Flow Synthesis of Difluoroamine Systems by Direct Fluorination

Christopher B. McPake A, Christopher B. Murray B C and Graham Sandford A C

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 http://dx.doi.org/10.1071/CH12381
Submitted: 15 August 2012  Accepted: 27 September 2012   Published: 17 January 2013


 
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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 | CAS |

[4]  G. Sandford, J. Fluor. Chem. 2007, 128, 90.
         | CrossRef | CAS |

[5]  R. D. Chambers, M. A. Fox, D. Holling, T. Nakano, T. Okazoe, G. Sandford, Lab Chip 2005, 5, 191.
         | CrossRef | CAS |

[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 | CAS |

[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 | CAS |

[9]  D. Holling, G. Sandford, A. S. Batsanov, D. S. Yufit, J. A. K. Howard, J. Fluor. Chem. 2005, 126, 1377.
         | CrossRef | CAS |

[10]  R. D. Chambers, M. P. Greenhall, J. Hutchinson, Tetrahedron 1996, 52, 1.
         | CrossRef | CAS |

[11]  R. D. Chambers, M. A. Fox, G. Sandford, Lab Chip 2005, 5, 1132.
         | CrossRef | CAS |

[12]  K. Baum, J. Am. Chem. Soc. 1968, 90, 7083.
         | CrossRef | CAS |

[13]  R. K. Belter, J. Fluor. Chem. 2012, 137, 73.
         | CrossRef | CAS |

[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 | CAS |

[16]  R. D. Dresdner, F. N. Tlumac, J. A. Young, J. Am. Chem. Soc. 1960, 82, 5831.
         | CrossRef | CAS |

[17]  W. P. Graham, J. P. Freeman, J. Am. Chem. Soc. 1967, 89, 716.
         | CrossRef | CAS |

[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 | CAS |

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

[20]  S. F. Reed, R. D. Shoults, J. Org. Chem. 1972, 37, 3326.
         | CrossRef | CAS |

[21]  C. M. Sharts, J. Org. Chem. 1968, 33, 1008.
         | CrossRef | CAS |

[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 |

[24]  T. Takagi, M. Tamura, M. Shibakami, H. Quan, A. Sekiya, J. Fluor. Chem. 2000, 101, 15.
         | CrossRef | CAS |

[25]  G. K. S. Prakash, G. A. Olah, M. Etzkorn, K. O. Christe, S. Schneider, A. Vij, Chem. Commun. 2002, 1712.
         | CrossRef | CAS |

[26]  C. L. Coon, M. E. Hill, D. L. Ross, J. Org. Chem. 1968, 33, 1387.
         | CrossRef | CAS |

[27]  M. W. Lerom, H. M. Peters, D. L. Ross, M. E. Hill, J. Dick, J. Chem. Eng. Data 1974, 19, 389.
         | CrossRef | CAS |

[28]  R. K. Belter, J. Fluor. Chem. 2011, 132, 961.
         | CrossRef | CAS |

[29]  C. A. Hargreaves, G. Sandford, R. Slater, D. S. Yufit, J. A. K. Howard, A. Vong, Tetrahedron 2007, 63, 5204.
         | CrossRef | CAS |

[30]  G. Sandford, R. Slater, D. S. Yufit, J. A. K. Howard, A. Vong, J. Org. Chem. 2005, 70, 7208.
         | CrossRef | CAS |

[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 | CAS |

[34]  R. D. Chambers, P. A. Martin, J. S. Waterhouse, D. L. H. Williams, B. Anderson, J. Fluor. Chem. 1982, 20, 507.
         | CrossRef | CAS |

[35]  G. M. Brooke, J. Chem. Soc. 1961, 802.
         | CrossRef | CAS |

[36]  L. J. Belf, M. W. Buxton, J. F. Tilney-Bassett, Tetrahedron 1967, 23, 4719.
         | CrossRef | CAS |

[37]  R. D. Chambers, J. Hutchinson, G. Sandford, J. Fluor. Chem. 1999, 100, 63.
         | CrossRef | CAS |

[38]  R. J. Koshar, D. R. Husted, C. D. Wright, J. Org. Chem. 1967, 32, 3859.
         | CrossRef | CAS |

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


   
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