Title | The photochemistry of trans-1,4,4,4-tetraphenylbut-2-en-1-one: A highly efficient aryl migration (type B) enone photorearrangement |
Publication Type | Journal Article |
Year of Publication | 2003 |
Authors | Scheffer, JR, Vishnumurthy, K |
Journal | Canadian Journal of Chemistry-Revue Canadienne De Chimie |
Volume | 81 |
Pagination | 705-708 |
Date Published | Jun |
Type of Article | Article |
ISBN Number | 0008-4042 |
Keywords | aryl 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. |
URL | <Go to ISI>://000184472400035 |
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