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Communication | Special issue | Vol 17, No. 1, 1982, pp.139-150
Published online, 1st January, 1970
DOI: 10.3987/S-1982-01-0139
Photolysis of Homoconjugated Allene Ketones

Walentina Kudrawcew, Bruno Frei, Hans Richard Wolf, and Oskar Jeger*

*Laboratorium für Organische, Eidgenössischen Technischen Hochschule, Universitatstrasse 16,8092 Zürich, Switzerland

Abstract

UV-Irradiation (λ>280 nm) of the homoconjugated allene ketones 4 and 5 gives, in addition to small amounts of the ketodienes 8 and 17 (1,3-acyl shift), the enol ethers 9, 10 and 18, 19 respectively (cyclization process followed by 1,5-H-shift). However, on T-sensitization in acetone, 4 forms the spirodioxetane 13 in high yield. Irradiation of 4 in 2-propanol or ethanol affords the acetals 11 and 12.