Investigating the Arenyl-Diene Double [3 + 2] Photocycloaddition reaction

Penkett, Clive S, Woolford, Jason A, Read, Timothy W and Kahan, Rachel J (2011) Investigating the Arenyl-Diene Double [3 + 2] Photocycloaddition reaction. The Journal of Organic Chemistry, 76 (5). pp. 1295-1304. ISSN 0022-3263

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Abstract

The double [3 + 2] photocycloaddition reaction involving arenyl−dienes has been used to assemble seven separate [5.5.5.5] fenestrane structures that include ether and aza variants. The primary photolysis step was a meta photocycloaddition reaction, while a secondary photocycloaddition step formed the fenestrane structure. Investigations involving the insertion of an additional methylene group into the basic arenyl−diene skeleton failed to afford the desired [5.5.5.6] fenestrane structure. The presence of an oxime moiety in the aromatic photosubstrate allowed the primary photolysis step to take place; however, an attempted secondary photocycloaddition reaction involving the oxime did not provide the intended polyheterocyclic fenestrane. An alternative strategy to form various “criss-cross” double meta photocycloadducts was investigated and led to the discovery of a Paterno−Büchi cycloaddition reaction between acetone and an angular meta photocycloadduct. Other novel thermally and photochemically mediated skeletal rearrangement reactions were also recorded.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: Rachel Kahan
Date Deposited: 27 Feb 2013 11:41
Last Modified: 07 Mar 2017 07:12
URI: http://sro.sussex.ac.uk/id/eprint/43833

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