Tetrahedron p. 315 - 326 (1984)
Update date:2022-08-11
Topics:
Arnaud, R.
Dussauge, A.
Faucher, H.
Subra, R.
Vidal, M.
Vincens, M.
The solvolysis in acid solution of allylic halides and acetates of methylenecyclopropanes and cyclopropylmethanes does not lead to ring opening when there is an ethoxycarbonyl substituent on the ring methylene.Only the cyclopropenyl derivative is obtained.A study of the electronic structure and the geometry of the possible allylic cation intermediate has been carried out using the MNDO method.In addition, the influence of the substituents on the ring opening of this cation has been examined.It appears that the ring opening is disfavoured upon substitution of an alkyl group by alkoxymethyl on the ring methylene group.
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