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

journal contribution
posted on 2023-06-08, 14:31 authored by Clive S Penkett, Jason A Woolford, Timothy W Read, Rachel J Kahan
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-Bu¨chi cycloaddition reaction between acetone and an angular meta photocycloadduct. Other novel thermally and photochemically mediated skeletal rearrangement reactions were also recorded.

History

Publication status

  • Published

File Version

  • Published version

Journal

The Journal of Organic Chemistry

ISSN

0022-3263

Publisher

American Chemical Society

Issue

5

Volume

76

Page range

1295-1304

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2013-02-27

First Compliant Deposit (FCD) Date

2013-02-27

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