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Photoaddition Reactions of 5‐Fluoro‐4,4‐dimethyl‐2‐cyclopentenone
Author(s) -
Thi Giao Vo,
Margaretha Paul
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590638
Subject(s) - chemistry , cyclopentenone , cyclopentene , cyclohexane , yield (engineering) , acetonitrile , medicinal chemistry , dimethyl ether , 2 butene , photochemistry , organic chemistry , catalysis , materials science , metallurgy
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.