ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
On 1,2-Dithiacyclopentenes, XXVI1). - Ring Cleavage of 5-Chloro-3H-1,2-dithiol-3-ones by Grignard Compounds5-Chloro-4-phenyl-3H-1,2-dithiol-3-one (1) and 4,5-dichloro-3H-1,2-dithiol-3-one (2) are cleaved by Grignard compounds at the S-S-bond with formation of intermediates which subsequently react to give sulfur heterocycles: Stereoisomeric 1,3-dithietanediylidene bis-(phenylthioacetic acid S-esters) 6 are obtained from 1, and 2-chloro-2-(dithiolidene)thioacetic acid S-esters 12 from 2. Reactions of 6 and 12 with nucleophilic compounds have been studied. The 1,3-dithietanes 6 are cleaved by amines with formation of monothiomalondiamides.
Notes:
5-Chlor-4-phenyl-3H-1,2-dithiol-3-on (1) und 4,5-Dichlor-3H-1,2-dithiol-3-on (2) werden durch Grignard-Verbindungen an der S-S-Bindung zu Primärprodukten gespalten, die zu Schwefelheterocyclen weiterreagieren: Aus 1 werden stereoisomere 1,3-Dithietandiylidenbis-(phenylthioessigsäure-S-ester) 6, aus 2 2-Chlor-2-(dithioliden)thioessigsäure-S-ester 12 erhalten. - Umsetzungen von 6 und 12 mit nucleophilen Partnern wurden untersucht. Amine spalten die 1,3-Dithietane 6 zu Monothiomalondiamiden 10.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197419740812
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