Generation, observation, and free radical reactivity of aliphatic bisketenes: the solution to a long-standing problem.
[reaction: see text] Bisketenes O=C=CH(CH(2))(n)()CH=C=O (1b,c,d, n = 4, 3, 6) and (E)-O=C=CHCH=CHCH=C=O (E-13) were generated in solution by dehydrochlorination of bis(acyl chlorides) and by photochemical Wolff rearrangements and identified by their characteristic IR signals. The bisketenes react with aminoxyl radicals to give tetraaddition products for 1b and conjugate 1,6-diaddition for E-13.
Allen
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AD
Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
Fenwick
M H
MH
Jabri
A
A
Rangwala
H
H
Saidi
K
K
Tidwell
T T
TT