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Chemistry of Sulfonate‐ and Sulfonamide‐Stabilized Carbanions − The CSIC Reactions
Author(s) -
Postel Denis,
Van Nhien Albert Nguyen,
Marco José L.
Publication year - 2003
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/ejoc.200300170
Subject(s) - chemistry , carbanion , sulfonamide , intramolecular force , ring (chemistry) , sulfonate , sulfone , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry , sodium
Abstract In this account we review the varied, but extensively documented reactions affording acyclic alkanesulfonates, alkanesulfonamides, and heterocyclic ring systems (sultones, 1,2‐oxathiole S , S ‐dioxides, sultams, and 2,3‐dihydroisothiazole S , S ‐dioxides) from conveniently functionalized alkanesulfonates or alkanesulfonamides, by a general procedure that we have named and classified as CSIC reactions both as intermolecular [ C arbanion‐mediated S ulfonate (or S ulfonamide) I ntermolecular C oupling] and as intramolecular [ C arbanion‐mediated S ulfonate (or S ulfonamide) I ntramolecular C yclization] variants of the conversion. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)