CYCLOHEXANE COMPOUNDS: V. THE REACTION OF 1-METHOXYCYCLOHEXENE-2 WITH AQUEOUS N-BROMOSUCCINIMIDE. THE 1-METHOXY-2-BROMO-3-HYDROXYCYCLOHEXANES

Authors
  1. Bannard, R.A.B.
  2. Casselman, A.A.
  3. Hawkins, L.R.
Corporate Authors
Defence Chemical Biological and Radiation Labs, Ottawa ONT (CAN)
Abstract
Interaction of 1-methoxycyclohexane-2 and aqueous N-bromosuccinimide gave a mixture of stereoisomeric bromohydrins, which, on treatment with aqueous sodium hydroxide, furnished 1beta-methoxy-2alpha,3alpha-epoxycyclohexane (I) and 1alpha-methoxy-2alpha,3alpha-epoxycyclohexane (II) in the ratio 3:1. The mixture from the N-haloimide-olefin reaction was separated by preparative vapor phase chromatography into three isomeric bromohydrins, 1alpha-methoxy-2alpha-hydroxy-3beta-bromocyclohexane (IV), 1alpha-methoxy-2alpha-bromo-3alpha-hydrocyclohexane (V), and 1alpha-methoxy-2beta-bromo-3alpha-hydrocyclohexane (VI) in the relative proportions 1:10:4. The 3-bromo isomer IV was identified by comparison with an authentic specimen prepared by the action of hydrobromic acid on oxide II. TRUNCATED
Report Number
DCBRL-457 — Reprint: Previously catalogued as DSIS 65-14927
Date of publication
01 Jan 1965
Number of Pages
12
Reprinted from
Canadian Journal of Chemistry, vol 43, 1965, p 2398-2407
DSTKIM No
89-01255
CANDIS No
59187
Format(s):
Hardcopy;Originator's fiche received by DSIS

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