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Intramolecular [2 + 2]-Photocycloadditions of 6-Allyl-2-cyclohexenones. Formation of Tricyclo[3.3.1.02,7]nonan-6-ones and Tricyclo[4.2.1.03,8]nonan-7-ones

✍ Scribed by Wolfgang Fröstl; Paul Margaretha

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
304 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Alkylation of 4,4,6‐trimethyl‐2‐cyclohexenone (1) in toluene in the presence of sodium bis(trimethylsilyl)amide proceeds smoothly to give high yields of compounds 2. Irradiation (λ= 366 nm) of the 6‐allyl‐4,4,6‐trimethyl‐2‐cyclohexenones 2a–c yields mixtures of the isomeric tricyclo‐nonanones 3 and 4, the product ratio depending on the substituent R' of the allylic side chain and on the solvent. The quantum yields for the cyclizations are given.

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