Photochemical Selenosulfonation of Tricyclo[4.1.0.02,7]heptane Derivatives

Se -Phenyl methane-, benzene-, and 4-methylbenzenesulfonoselenoates PhSeSO 2 R (R = Me, Ph, 4-MeC 6 H 4 ) react with 1-X-tricyclo[4.1.0.0 2,7 ]heptanes (X = Me, Ph, SiMe 3 ) under photochemical initiation to give products of addition at the C 1 –C 7 central bicyclobutane bond with a bicyclo[3.1.1]he...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-06, Vol.56 (6), p.1006-1013
Main Authors: Kostryukov, S. G., Masterova, Yu. Yu, Burtasov, A. A., Romanova, E. V.
Format: Article
Language:English
Subjects:
Benzene
Chemistry
Chemistry and Materials Science
Heptanes
Organic Chemistry
Stereochemistry
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Summary:Se -Phenyl methane-, benzene-, and 4-methylbenzenesulfonoselenoates PhSeSO 2 R (R = Me, Ph, 4-MeC 6 H 4 ) react with 1-X-tricyclo[4.1.0.0 2,7 ]heptanes (X = Me, Ph, SiMe 3 ) under photochemical initiation to give products of addition at the C 1 –C 7 central bicyclobutane bond with a bicyclo[3.1.1]heptane (norpinane) skeleton, where the R-sulfonyl group is attached to C 7 and is oriented syn and the phenylselanyl group on C 6 can occupy both syn and anti positions. Radical mechanism of the reaction and its stereochemistry are discussed.
ISSN:1070-4280
1608-3393
DOI:10.1134/S107042802006007X