Journal of the Chemical Society. Perkin transactions I p. 2033 - 2048 (1980)
Update date:2022-08-04
Topics:
Laird, Trevor
Ollis, W. David
Sutherland, Ian O.
The base catalysed rearrangements of the cations (7), (17), (22), and (27) gave the enamines (9), (18), (23), and (28), which on hydrolysis yielded the aldehyde (10), (19), (24), and (29) respectively.The reactions are shown to be concerted <5,4> sigmatropic rearrangements proceeding via a nine-membered transition state involving 10? electrons.The base catalysed rearrangements of the 3-phenylprop-2-ynyl (pentadienyl) ammonium cations (51), (52), (60), and (61), however yield only the products of <1,2>, <3,2>, and <5,2> sigmatropic rearrangements.
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Doi:10.1248/cpb.35.3859
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