91597-63-6Relevant articles and documents
ADDITION REACTIONS TO BICYCLOBUTANE DERIVATIVES. THE REGIOSELECTIVITY OF THE ADDITION OF METHANOL AND METHANETHIOL TO 3-VINYLCYCLOBUTANE-1-CARBONITRILE
Razin, V. V.,Vasin, V. A.
, p. 669 - 673 (2007/10/02)
3-Vinylcyclobutane-1-carbonitrile adds anionoid nucleophiles (sodium methoxide and methanethiolate) in methanol strictly regioselectively at the central C-C bond with the formation of 3-vinyl-3-methoxy(methylthio)cyclobutane-1-carbonitrile (1,3-addition).The same substrate adds methanol under the catalytic influence of perchloric acid with the formation of both the 1,3-addition product and the 1,5-addition product, i.e., 3-(2-methoxyethylidene)cyclobutane-1-carbonitrile (with the regioisomers in a ratio of 3:2).