ISSN:
0009-2940
Keywords:
Dithiolactones
;
Electroreduction
;
Haloalkanedithioates
;
Thioacetals, semicyclic
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230825