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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

New Elements on the Behaviour of a Bissulfinylmethyl Radical*

Rocio Martinez Mallorquin A , Guillaume Vincent A , Etienne Derat A , Max Malacria A , Jean-Philippe Goddard A B and Louis Fensterbank A B
+ Author Affiliations
- Author Affiliations

A Institut Parisien de Chimie Moléculaire (UMR CNRS 7201) – FR2769 UPMC Univ Paris 06, 4 place Jussieu, C. 229, 75005 Paris, France.

B Corresponding authors. Email: jean-philippe.goddard@upmc.fr; louis.fensterbank@upmc.fr

Australian Journal of Chemistry 66(3) 346-353 https://doi.org/10.1071/CH12545
Submitted: 13 December 2012  Accepted: 1 February 2013   Published: 7 March 2013

Abstract

In this article, we have studied the generation of a bissulfinylmethyl radical from the corresponding TEMPO and phenylselenyl bissulfoxide precursors. No univocal formation of the bissulfinylmethyl radical has been observed. Instead, complex mixtures have been obtained in thermal or photochemical conditions, showing prominent C–S homolytic bond cleavage.


References

[1]  J.-P. Goddard, C. Gomez, F. Brebion, S. Beauvière, L. Fensterbank, M. Malacria, Chem. Commun. 2007, 2929.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  J. H. Byers, G. C. Lane, J. Org. Chem. 1993, 58, 3355.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  C. Wetter, K. Jantos, K. Woithe, A. Studer, Org. Lett. 2003, 5, 2899.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) A. J. Herrera, A. Studer, Synthesis 2005, 1389.
      (b) M. de Greef, S. Z. Zard, Tetrahedron 2004, 60, 7781.
         | Crossref | GoogleScholarGoogle Scholar |

[5]     (a) C. Chatgilialoglu, in The Chemistry of Sulphones and Sulphoxides (Eds S. Patai, Z. Rappoport, C. J. M. Stirling) 1988, pp. 1081–1087 (John Wiley & Sons Ltd.: New York, NY).
      (b) A. P. Darmanyan, D. D. Gregory, Y. Guo, W. S. Jencks, J. Phys. Chem. A 1997, 101, 6855.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. S. Grainger, B. Patel, B. M. Kariuki, Angew. Chem. Int. Ed. 2009, 48, 4832.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) P. T. Lynett, K. Butts, V. Vaidya, G. E. Garrett, D. A. Pratt, Org. Biomol. Chem. 2011, 9, 3320.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  G. Gryn’ova, K. U. Ingold, M. L. Coote, J. Am. Chem. Soc. 2012, 134, 12979.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  P. Carloni, E. Damiani, M. Iacussi, L. Greci, P. Stipa, D. Cauzi, C. Rizzoli, P. Sgarabotto, Tetrahedron 1995, 51, 12445.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  F. Brebion, J. P. Goddard, L. Fensterbank, M. Malacria, Synthesis 2005, 2449.

[9]  R. A. Aitken, M. J. Drysdale, G. Ferguson, A. J. Lough, J. Chem. Soc. Perkin Trans. 1 1998, I, 875.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  For the formation of carbene intermediates under radical conditions, see: K. J. Tan, U. Wille, Chem. Comm. 2008, 6239.

[11]  A. Christoforou, G. Nicolaou, Y. Elemes, Tetrahedron Lett. 2006, 47, 9211.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  (a) Z. Blum, K. Nyberg, Acta Chem. Scand. B 1981, 35b, 743.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) J. Zakrzewski, M. Krawczyk, Heteroatom Chem. 2006, 17, 393.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  S. K. Su, J. P. Zhang, X. R. Liang, Org. Prep. Proced. Int. 2006, 38, 404.

[14]  M. Sprecher, E. Nov, Synth. Commun. 1992, 22, 2949.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  (a) Z isomer: Y. Xu, W. Hao, D. Wang, M. Cai, Heteroatom Chem. 2008, 19, 639.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) E isomer: Y. Zheng, X. Du, W. Bao, Tetrahedron Lett. 2006, 47, 1217.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  (a) A. Toshimitsu, H. Abe, C. Hirosawa, K. Tamao, J. Chem. Soc. Perkin Trans. 1 1994, 3465.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) M. Kameyama, N. Kamigata, M. Kobayashi, J. Org. Chem. 1987, 52, 3312.
         | Crossref | GoogleScholarGoogle Scholar |