Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
REGIOSPECIFIC NEIGHBORING-GROUP PARTICIPATION BY DITHIOCARBAMATE FUNCTION DURING BROMINATION OF γ-SUBSTITUTED S-ALLYL N,N-DIMETHYLDITHIOCARBAMATES
Kazuhisa HirataniTakeshi NakaiMakoto Okawara
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1974 Volume 3 Issue 9 Pages 1041-1044

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Abstract

Bromination of the title compounds 1 resulted in the formation of the corresponding 2-dimethylamino-4-bromomethyl-1,3-dithiolan-2-ylium bromide (2) via regiospecific (S-5) participation by the dithiocarbamate function, irrespective of substitution on the γ-carbon atom. This is in contrast to the C-protonation of 1 in which the ratio of S-5 vs. S-6 depends on the γ-substitution.

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