Two directions of heterocyclization in the reactions of dimethyl bicyclo[2.2.2]oct-5-ene-endo-2,endo-3-dicarboxylate with hetarenesulfenyl chlorides

A reaction of dimethyl bicyclo[2.2.2]oct-5-ene- endo -2, endo -3-dicarboxylate with 1,3-benzо- thiazole-2- and 3-methoxycarbonylpyridine-2-sulfenyl chlorides leads to two types of heterocyclization products, which are formed through the ring closure by the oxygen atom of the carbоmethoxy group and/o...

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Published inRussian chemical bulletin Vol. 67; no. 3; pp. 525 - 529
Main Authors Borisov, A. V., Osmanov, V. K., Borisova, G. N., Matsulevich, Zh. V., Fukin, G. K.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.03.2018
Springer Nature B.V
Subjects
ATOMS
CHEMICAL REACTIONS
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
CHLORIDES
Full Articles
Inorganic Chemistry
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
NITROGEN
OCTANE
Organic Chemistry
OXYGEN
THIAZOLES
electrophilic addition
heterocyclization
sulfenyl chlorides
bicyclo[2.2.2]octane derivatives
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Summary:A reaction of dimethyl bicyclo[2.2.2]oct-5-ene- endo -2, endo -3-dicarboxylate with 1,3-benzо- thiazole-2- and 3-methoxycarbonylpyridine-2-sulfenyl chlorides leads to two types of heterocyclization products, which are formed through the ring closure by the oxygen atom of the carbоmethoxy group and/or by the nitrogen atom of the hetaryl fragment of the sulfenylating agent. The product ratio is affected by the medium nature and structural features of sulfenyl chlorides.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-018-2105-8