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Formation of Cyclic Sulfinates and Sulfinamides through Homolytic Substitution at the Sulfur Atom
Author(s) -
Coulomb Julien,
Certal Victor,
Fensterbank Louis,
Lacôte Emmanuel,
Malacria Max
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503369
Subject(s) - chemistry , heteroatom , homolysis , sulfur , substitution (logic) , ring (chemistry) , alkyl , radical , azobisisobutyronitrile , stereocenter , chirality (physics) , organic chemistry , catalysis , enantioselective synthesis , computer science , polymerization , programming language , polymer , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Ring road : Cyclic sulfinates and sulfinamides can be synthesized by homolytic substitution to give alkyl and benzofused families of compounds. The presence of an additional heteroatom in the ring allows the preparation of sulfur‐based heterocycles that are useful synthetic intermediates (see scheme). The stereogenic sulfur atom transfers its chirality to prochiral radicals. TTMSS=tris(trimethylsilyl)silane, AIBN=azobisisobutyronitrile.