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Photocycloaddition Reactions of 5,5-Dimethyl-3-(3-methylbut-3-en-1-ynyl)cyclohex-2-en-1-one

✍ Scribed by Inga Inhülsen; Jürgen Kopf; Paul Margaretha

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
197 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The title cyclohexenone 1d undergoes photodimerization selectively at the exocyclic CC bond to give a 1 : 1 mixture of 1,2‐dialkynyl‐1,2‐dimethylcyclobutanes 6 and 7. On irradiation in the presence of 2,3‐dimethylbuta‐1,3‐diene, 1d affords bicyclo[8.4.0]tetradeca‐1,2,3,7‐tetraen‐11‐one 9. This – formal – (6+4)‐cycloadduct undergoes quantitative isomerization to 3‐cycloheptadienyl‐2,5,5‐trimethylcyclohex‐2‐enone 11 on treatment with basic silica gel.

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