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Radical β‐Elimination of a Sulfinyl Group to Afford Allenes
Author(s) -
Mouriès Virginie,
Delouvrié Bénédicte,
Lacôte Emmanuel,
Fensterbank Louis,
Malacria Max
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200206)2002:11<1776::aid-ejoc1776>3.0.co;2-6
Subject(s) - chemistry , group (periodic table) , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry
An unprecedented radical β‐elimination of vinyl sulfoxides has opened a new route to functionalized allenes. The radical precursors were obtained in two steps from a carbonyl derivative and a vinyl sulfoxide. The radical translocation stratagem could also be used to trigger the β‐elimination of the sulfinyl radical. Variation of the nature of the sulfur group on a common precursor gave no allene with the thio, sulfonyl, and iminosulfinyl moieties, in contrast to the analogous vinyl sulfoxide and vinylsulfimide precursors. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)