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Neighboring Group and Substituent Effects in Organosulfur Compounds
Author(s) -
Gundermann K. D.
Publication year - 1963
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196306741
Subject(s) - thioether , chemistry , organosulfur compounds , substituent , reactivity (psychology) , nucleophile , nucleophilic substitution , double bond , epoxide , leaving group , medicinal chemistry , halide , stereochemistry , organic chemistry , sulfur , catalysis , medicine , alternative medicine , pathology
Thioether groups participate in nucleophilic substitution reactions at adjacent carbon atoms, in the addition of alkane and arenesulfenyl halides onto olefinic double bonds, and in elimination reactions which lead to olefins and which proceed via intermediate episulfonium ions. Studies of alkylthioacrylic acid derivatives, which are readily synthetized because of the neighboring group effect, show that the presence of thioether groups in the α‐position of acrylic acid systems leads to particularly high reactivity in “head‐to‐head” dimerizations.