Issue 0, 1981
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Base catalysed rearrangements involving ylide intermediates. Part 11. Rearrangements of 3-phenylprop-2-ynylammonium ylides

Sivapathasuntharam Mageswaran,   W. David Ollis,   Dolores A. Southam,   Ian O. Sutherland  and  Yodhathai Thebtaranonth  

Abstract

The propynylammonium salt (5) reacts with aqueous sodium hydroxide to give the allene (7) and a new ylide (11). The simultaneous formation of (7) and (11) suggests that the apparent [3,2] sigmatropic rearrangement of the propynyl ylide (6) to the allene (7) may involve a two-stage mechanism. The reactions of the ylide (11) are described, as are those of the allene (7) and a number of similar allenes derived from the propynylammonium salts (23) and (27). Three types of reaction are recognised for the allenes including a novel [1,3] rearrangement involving the migration of a dimethylamino-group. The base catalysed rearrangements of the bicyclic propynylammonium salts (52) and (56) do not show the inhibition expected for concerted [3,2] sigmatropic rearrangements in such bicyclic systems. This observation provides further evidence for a two-stage mechanism for the apparent [3,2] sigmatropic rearrangement of propynylammonium ylides.

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Article information

DOI
https://doi.org/10.1039/P19810001969
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 1969-1980

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Base catalysed rearrangements involving ylide intermediates. Part 11. Rearrangements of 3-phenylprop-2-ynylammonium ylides

S. Mageswaran, W. D. Ollis, D. A. Southam, I. O. Sutherland and Y. Thebtaranonth, J. Chem. Soc., Perkin Trans. 1, 1981, 1969 DOI: 10.1039/P19810001969

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