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Photoaddition Reactions of 5-Fluoro-4,4-dimethyl-2-cyclopentenone

✍ Scribed by Giao Vo Thi; Paul Margaretha

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

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✦ Synopsis

Abstract

The photoaddition of 5‐fluoro‐4,4‐dimethyl‐2‐cyclopentenone (4) to 2,3‐dimethyl‐2‐butene leads specifically (in cyclohexane) and selectively (in acetonitrile) to the formation of the oxetanes 16. The title compound is compared in its behaviour to the analogous 6‐fluoro‐4,4‐dimethyl‐2‐cyclohexenone (1) and both α'‐fluoro‐4,4‐dimethyl‐2‐cycloalkenones in turn are compared to the corresponding 2‐cycloalkenones (6 and 3) and 4,4‐dimethyl‐2‐cycloalkenones (5 and 2). The quantum yield for the addition of these enones to 2,3‐dimethyl‐2‐butene and to cyclopentene are discussed.

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