Volume 90, Issue 9 pp. 1667-1671
Research Article

A First Approach to the cis-trans-cis-Photocyclodimers of 1,2-Naphthoquinone

Kerstin Schmidt

Kerstin Schmidt

Chemistry Department, University of Hamburg, Martin-Luther-King Platz 6, D-20146 Hamburg, (phone: +4940428384316; fax: +4940428385592)

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Juergen Kopf

Juergen Kopf

Chemistry Department, University of Hamburg, Martin-Luther-King Platz 6, D-20146 Hamburg, (phone: +4940428384316; fax: +4940428385592)

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Paul Margaretha

Paul Margaretha

Chemistry Department, University of Hamburg, Martin-Luther-King Platz 6, D-20146 Hamburg, (phone: +4940428384316; fax: +4940428385592)

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First published: 25 September 2007
Citations: 4

Abstract

On irradiation (λ=350 nm), 1,2-naphthoquinone (=naphthalene-1,2-dione) monoacetals 1 are converted quantitatively to mixtures of the cis-trans-cis-photocyclodimers 2 and 3. Careful hydrolysis of each of the (parent) pentacyclic diacetals 2a and 3a affords the – rather unstable – compounds 4 and 5, respectively.

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