✦ LIBER ✦

Steric and electronic factors in the addition of phenylsulfinyl carbene to methyl-substituted ethylenes.

✍ Scribed by Clifford G. Venier; Mark A. Ward

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 243 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85597-0

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✦ Synopsis

The unusual stability of phenylsulfinyl carbene, signalled by (1) the ease by which it is formed unimolecularly from phenyl diazomethyl sulfoxide, (2) the lack of C-H insertion reactions, and (3) the high degree of stereoselectivity in cycloaddition to Z-2-butene and cyclohexene, 2 strongly suggests that the sulfinyl sulfur can stabilize the carbene by donation of its lone electron pair into the empty orbital of the carbenic carbon, a conclusion at odds with the generally held view that the sulfinyl function is an electron-withdrawing group.3

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