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Elektroreduktion organischer Verbindungen, 16. Elektroreduktion von ω‐Halogenalkandithiosäure‐methylestern
Author(s) -
Böge Askan,
Voß Jürgen
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230825
Subject(s) - chemistry , ketene , medicinal chemistry , electrochemistry , methanol , selectivity , intramolecular force , radical , organic chemistry , catalysis , electrode
Intramolecular cyclization occurs on electroreduction of the methyl ‐haloalkanedithioates 1 in methanol. The expected semicyclic thioacetals 2 are formed according to an ECEH mechanism. The biheterocycles 12 result from dimerization of intermediate radicals whereas the semicyclic ketene dithio‐acetals 13 are formed by non‐electrochemical processes. The 2‐(methylthio)thiolanes 2 a and 16 are obtained with much higher yields and better selectivity by co‐electroreduction of the ‐dithio‐lactones 15 in the presence of dimethyl sulfate.