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The photochemistry of trans-1,4,4,4-tetraphenylbut-2-en-1-one: A highly efficient aryl migration (type B) enone photorearrangement

TitleThe photochemistry of trans-1,4,4,4-tetraphenylbut-2-en-1-one: A highly efficient aryl migration (type B) enone photorearrangement
Publication TypeJournal Article
Year of Publication2003
AuthorsScheffer, JR, Vishnumurthy, K
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume81
Pagination705-708
Date PublishedJun
Type of ArticleArticle
ISBN Number0008-4042
Keywordsaryl migration, ASYMMETRIC INDUCTION, di-pi-methane, enone, EXPLORATORY ORGANIC PHOTOCHEMISTRY, MECHANISM, MIGRATION, PHENYL, PHOTOCHEMISTRY, PHOTOCYCLIZATION, REARRANGEMENT, STATE
Abstract

Photolysis of trans-1,4,4,4-tetraphenylbut-2-en-1-one (3) in acetonitrile or benzene leads to trans-cis isomerization (7) along with rearrangement to trans-1 -benzoyl-2,2,3-triphenylcyclopropane(8). Formation of the latter product represents a new example of the aryl migration (type B) enone photorearrangement reaction first reported by Zimmerman and co-workers for 4,4-diphenylcyclohex-2-en-1-one (1). The quantum yield in the case of enone 3 (0.4) is approximately 10 times greater than that for 4,4,-diphenylcyclohex-2-en-1-one, a result that is ascribed to steric acceleration of phenyl migration from the triphenylmethyl group plus greater resonance stabilization of the intermediate biradical.

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