Journal of the Chemical Society. Chemical communications p. 1033 - 1034 (1989)
Update date:2022-08-28
Topics:
Banks, Malcolm R.
Cadogan, J. I. G.
Gosney, Ian
Hodgson, Philip K. G.
Jack, Audrey G. C.
Rodger, David R.
Pyrolytic expulsion of ethylene from 2-neopentoxy-1,3,2-dioxaphospholane in the gas phase yields a virtually quantitative mixture of 2-methylbut-1-ene and its more stable isomer, 2-methylbut-2-ene in the ratio 2:1; this can be rationalised, using deuterium-labelling studies, as being formed from a thermally generated metaphosphate by a cyclic, concerted elimination reaction involving, as the key step, an unusual 1,2-methyl shift induced by competing α- and γ-hydrogen abstraction reactions with loss of metaphosphoric acid.
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