Polar effects on di-.pi.-methane rearrangements. Regiospecificity in the triplet-sensitized photoisomerizations of 2-cyanobenzonorbornadienes carrying methoxy aryl substituents

This reaction, known as the Zimmerman rearrangement, di‐π‐methane rearrangement, di‐π‐methane photorearrangement, or di‐π‐methane reaction, is a photochemical reaction of a molecular entity comprising two π‐systems separated by a saturated carbon atom (a sp 3 carbon, e.g. a methylene group) involving the migration of one π‐moiety bonded to the saturated carbon to other π‐moiety accompanied by the concomitant formation of a cyclopropane ring from the remaining π‐moiety and methylene group. This rearrangement has been reported to consist at least six versions and all these variants differ from each other. This rearrangement has high regiospecificity with a strong preference for migration of the less conjugated π‐moiety to the more conjugated one. This rearrangement has proven valuable in preparation of substituted cyclopropanes.

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ChemInform Abstract: POLAR EFFECTS ON DI‐Π‐METHANE REARRANGEMENTS. REGIOSPECIFICITY IN THE TRIPLET‐SENSITIZED PHOTOISOMERIZATIONS OF 2‐CYANOBENZONORBORNADIENES CARRYING METHOXY ARYL SUBSTITUENTS

Ku¹,

Paquette²,

Rozeboom³

et al. 1980

Chemischer Informationsdienst

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Polar effects on di-.pi.-methane rearrangements. Regiospecificity in the triplet-sensitized photoisomerizations of 2-cyanobenzonorbornadienes carrying methoxy aryl substituents

Cited by 11 publications

References 4 publications

The Di-π-methane Photorearrangement of 2,3-Disubstituted Benzobarrelenes and Benzonorbornadiene − Substituent Effects in Regioselectivity

The Di-π-methane Photorearrangement of 2,3-Disubstituted Benzobarrelenes and Benzonorbornadiene − Substituent Effects in Regioselectivity

Di‐Π‐Methane Rearrangement

ChemInform Abstract: POLAR EFFECTS ON DI‐Π‐METHANE REARRANGEMENTS. REGIOSPECIFICITY IN THE TRIPLET‐SENSITIZED PHOTOISOMERIZATIONS OF 2‐CYANOBENZONORBORNADIENES CARRYING METHOXY ARYL SUBSTITUENTS

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