Reductive cyclization of compounds with a CCl2CH2CCl(CH3)2 grouping

Autor: Kamyshova, A. A., Polishchuk, S. D., Chukovskaya, E. Ts., Freidlina, R. Kh.
Zdroj: Russian Chemical Bulletin; January 1977, Vol. 26 Issue: 1 p160-164, 5p
Abstrakt: 1.1,1,2-Trimethylcyclopropane (46%) and 1-chloro-1,2,2-trimethylcyclopropane (13%) were obtained from 2,2,4-trichloro-4-methylpentane, while 1-(ß-chloroethyl)-2,2-dimethylcyclopropane (18%), 1-chloro-1-(ß-chloroethyl)-2,2-dimethylcyclopropane (16%), and isobutylidenecyclopropane (25%) were obtained from 1,3,3,5-tetrachloro-5-methylhexane. As a result, it was shown that a chlorine atom, attached to a tertiary C atom, is involved in reductive cyclization.2.It was shown for the first time that the process has a stepwise course: 1,3-dechlorination occurs initially, which leads to the formation of chlorocyclopropanes. Then the chlorine atom in the chlorocyclopropane is either replaced by hydrogen or else it is dehydrochlorinated to a cyclopropane with an exocyclic multiple bond.
Databáze: Supplemental Index