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Stereoselective Radical Aryl Migration Reactions from Sulfur to Carbon
Author(s) -
Bossart Martin,
Fässler Roger,
Schoenberger Jan,
Studer Armido
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(200208)2002:16<2742::aid-ejoc2742>3.0.co;2-r
Subject(s) - chemistry , radical , aryl , sulfur , stereoselectivity , aryl radical , organic chemistry , carbon fibers , medicinal chemistry , photochemistry , catalysis , alkyl , materials science , composite number , composite material
Stereoselective aryl migration reactions from sulfur in sulfonates and sulfonamides to C ‐centered radicals are reported. The 1,5‐aryl migration from sulfur to differently substituted C ‐centered radicals could be performed with high yields and selectivities. Functionalized aryl groups could also be transferred by this new method. A model to explain the stereochemical outcome of the reaction is presented and some mechanistic aspects of this reaction are discussed. Aryl migration reactions from sulfur in sulfinates to carbon radicals were less efficient, and the corresponding migrations in aryl sulfoxides were not observed at all. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)