Photochemical transformations of the [4 + 2] dimeric adduct of 2-benzoylnorborna-2,5-diene and its derivatives

Venkataramani, P. S. ; Chandrasekaran, S. ; Swaminathan, S. (1975) Photochemical transformations of the [4 + 2] dimeric adduct of 2-benzoylnorborna-2,5-diene and its derivatives Journal of the Chemical Society, Perkin Transactions 1, 1975 (8). pp. 730-734. ISSN 0300-922X

Full text not available from this repository.

Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1975...

Related URL: http://dx.doi.org/10.1039/P19750000730

Abstract

Irradiation of the [4 + 2] dimeric adduct (7) of 2-benzoylnorborna-2,5-diene yields the [2 + 2] dimeric adduct (9). The head-head combination in structure (9) has been established by its conversion into the known 3,3'-Dibenzyl-2,2'-binorborn-5-ene (12). Irradiation of tetrahydro-derivative (8) of the adduct (7), however, gives the retrodiene product, 2-benzoylnorborn-2-ene (16), identified by comparison with synthetic material. The intermediacy of a cyclobutane (19) in the formation of compound (16) was ruled out by the isolation of the cyclobutanol (20) as the major product from irradiation of (19). mechanistic pathways for these transformations are discussed.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:70729
Deposited On:21 Nov 2011 05:24
Last Modified:13 Jul 2012 13:47

Repository Staff Only: item control page