The four trans chlorohydrins of 3-methoxycyclohexene

Publisher Website
Google Scholar
Abstract
Trans-3-Methoxycyclohexene oxide (II), when treated with ethereal hydrogen chloride, gives the chlorohydrin dl-1α-chloro-2β-hydroxy-3α-methoxycyclohexane (IVa), and the cis oxide III gives dl-1β-chloro-2α-hydroxy-3α-methoxycyclohexane (Va). The point of scission of the oxide ring (remote from the methoxyl) is therefore the same as in other reactions observed by ourselves and others. The reaction of 3-methoxycyclohexene (I) with N-chlorosuccinimide and water at 100° gives three chlorohydrins: dl-1β-chloro-2α-hydroxy-3α-methoxycyclohexane (VI), dl-2β-chloro-1α-hydroxy-3α-methoxycyclohexane (VIa), and dl-2α-chloro-1β-hydroxy-3α-methoxycyclohexene (VIIa) (approximately in the ratio 10:38:50, respectively). Two of the chlorohydrins were solids, and the homogeneity of the liquid isomers was demonstrated in several ways. The structures were proven by the nuclear magnetic resonance spectra of the p-nitrobenzoates, and by chemical methods. The results are of considerable interest with regard to the theory of addition and substitution reactions. There is a close parallel with the results in the bromohydrin series.

This publication has 0 references indexed in Scilit: