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Issue 3, 2002
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Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated syntheses

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Abstract

Synthetic routes to pure 1-phenylcyclohexa-2,5-diene-1-carboxylic acid and derived esters were developed. Esters containing appropriately unsaturated side chains generated the corresponding alkenyl radicals and hence gave good yields of 5-exo ring closure products in organotin-free reactions. Extrusion of phenyl radicals from the intermediate cyclohexadienyl type radicals was not observed, and this alternative β-scission did not compete under any conditions. Yields from alkylations of olefins in analogous intermolecular processes were, however, poor. As a spin-off from the research, it was found that 1-phenylcyclohexa-2,5-diene-1-carboxylic acid (6) was a useful source of hydroxyformyl (formate) radicals in organic solvents.

Graphical abstract: Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated syntheses

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Article information


Submitted
16 Nov 2001
Accepted
03 Dec 2001
First published
09 Jan 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 304-309
Article type
Paper

Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated syntheses

P. A. Baguley, L. V. Jackson and J. C. Walton, J. Chem. Soc., Perkin Trans. 1, 2002, 304
DOI: 10.1039/B110527M

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