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Article << Previous     |     Next >>   Contents Vol 66(3)

Kinetic Study of the Radical Azidation with Sulfonyl Azides*

Karin Weidner A and Philippe Renaud A B

A University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, CH-3012 Bern, Switzerland.
B Corresponding author. Email: philippe.renaud@ioc.unibe.ch

Australian Journal of Chemistry 66(3) 341-345 http://dx.doi.org/10.1071/CH12523
Submitted: 25 November 2012  Accepted: 18 December 2012   Published: 25 January 2013


 
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Abstract

Rate constants for the reaction between a secondary alkyl radical and two different sulfonyl azides were determined using bimolecular competing radical reactions. The rates of azidation were determined by competition with hydrogen atom transfer from tris(trimethylsilyl)silane ((TMS)3SiH) of the 4-phenylcyclohexyl radical. 3-Pyridinesulfonyl azide and trifluoromethanesulfonyl azide were found to have rate constants for azidation of 2 × 105 M–1 s–1 and 7 × 105 M–1 s–1 at 80°C, respectively.





References

[1]  Organic Azides: Syntheses and Applications (Eds S. Bräse, K. Banert) 2010 (Wiley: Chichester).

[2]  G. Lapointe, A. Kapat, K. Weidner, P. Renaud, Pure Appl. Chem. 2012, 84, 1633.
         | CrossRef | CAS |

[3]  P. Panchaud, L. Chabaud, Y. Landais, C. Ollivier, P. Renaud, S. Zigmantas, Chem. – Eur. J. 2004, 10, 3606.
         | CrossRef | CAS |

[4]  C. Ollivier, P. Renaud, J. Am. Chem. Soc. 2001, 123, 4717.
         | CrossRef | CAS |

[5]  C. Ollivier, P. Renaud, J. Am. Chem. Soc. 2000, 122, 6496.
         | CrossRef | CAS |

[6]  E. Nyfeler, P. Renaud, Org. Lett. 2008, 10, 985.
         | CrossRef | CAS |

[7]  A. Kapat, A. Konig, F. Montermini, P. Renaud, J. Am. Chem. Soc. 2011, 133, 13890.
         | CrossRef | CAS |

[8]  J. Waser, E. M. Carreira, in Organic Azides: Syntheses and Applications (Eds S. Bräse, K. Banert) 2010, pp. 95–111 (Wiley: Chichester).

[9]  B. Gaspar, J. Waser, E. M. Carreira, Synthesis 2007, 3839.
         | CAS |

[10]  J. Waser, H. Nambu, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 8294.
         | CrossRef | CAS |

[11]  P. Renaud, C. Ollivier, P. Panchaud, Angew. Chem. Int. Ed. 2002, 41, 3460.
         | CrossRef | CAS |

[12]  K. Weidner, A. Giroult, P. Renaud, J. Am. Chem. Soc. 2010, 132, 17511.
         | CrossRef | CAS |

[13]  P. Panchaud, C. Ollivier, P. Renaud, S. Zigmantas, J. Org. Chem. 2004, 69, 2755.
         | CrossRef | CAS |

[14]  N. Mantrand, P. Renaud, Tetrahedron 2008, 64, 11860.
         | CrossRef | CAS |

[15]  D. S. Masterson, J. P. Shackleford, Synlett 2007, 1302.
         | CrossRef | CAS |

[16]  M. Newcomb, in Encyclopedia of Radicals in Chemistry, Biology and Materials (Eds C. Chatgilialoglu, A. Studer) 2012, Vol. 1 (Basic Concepts and Methodologies), pp. 107–124 (John Wiley & Sons Ltd: Chichester).

[17]  H.-S. Dang, B. P. Roberts, J. Chem. Soc., Perkin Trans. 1 1996, 1493.
         | CrossRef | CAS |

[18]  S. Kim, G. H. Joe, J. Y. Do, J. Am. Chem. Soc. 1994, 116, 5521.
         | CrossRef | CAS |

[19]  L. Benati, G. Bencivenni, R. Leardini, M. Minozzi, D. Nanni, R. Scialpi, P. Spagnolo, G. Zanardi, J. Org. Chem. 2006, 71, 5822.
         | CrossRef | CAS |

[20]  C. Chatgilialoglu, Acc. Chem. Res. 1992, 25, 188.
         | CrossRef | CAS |

[21]  C. Chatgilialoglu, J. Dickhaut, B. Giese, J. Org. Chem. 1991, 56, 6399.
         | CrossRef | CAS |

[22]  P. Panchaud, P. Renaud, Adv. Synth. Catal. 2004, 346, 925.
         | CrossRef | CAS |

[23]  J. Raushel, S. M. Pitram, V. V. Fokin, Org. Lett. 2008, 10, 3385.
         | CrossRef | CAS |

[24]  K. Weidner, Ph.D. Thesis, 2010, Universität Bern.

[25]  S. Kobayashi, M. Yasuda, I. Hachiya, Chem. Lett. 1996, 25, 407.
         | CrossRef |


   
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