Accession Number : AD0450822


Title :   CYCLOHEXANE COMPOUNDS. III. THE 1-METHOXY AND 1-ETHOXY-2-HYDROXY-3-BROMOCYCLOHEXANES,


Corporate Author : DEFENCE CHEMICAL BIOLOGICAL AND RADIATION LABS OTTAWA (ONTARIO)


Personal Author(s) : Bannard, R A B ; Hawkins, L R


Report Date : 23 Feb 1961


Pagination or Media Count : 14


Abstract : 1ALPHA-Methoxy-2beta-hydroxy-3alpha-bromocyclohexane and 1alpha-methoxy-2alpha-hydroxy-3betabromocyclohexane have been prepared by the action of hydrobromic acid on 1beta-methoxy-2alpha, 3alpha-epoxycyclohexane and 1alpha-methoxy2alpha,3alpha-epoxycyclohexane respectively. Assignment of stereochemical configuration to 1alpha-methoxy-2beta-hydroxy-3alpha-bromocyclohexane was made by catalytic debromination of the phenyl- and 1-naphthyl-urethane to derivatives of 2beta-methoxy-1alpha-cyclohexanol. An alternative proof of sturcture was obtained by de-etherification of the bromohydrin to 3alpha-bromo-1alpha,2beta-cyclohexanediol, which was catalytically debrominated to 1alpha, 2beta-cyclohexanediol and oxidized via periodate to 2-bromoadipaldehyde, isolated as the bis-2,4-dinitrophenylhydrazone. The structure of 1alpha-methoxy-2alpha-hydroxy-3beta-bromocyclohexane was established by de-etherification to 3beta-bromo-1alpha,2alpha-cyclohenanediol, which was oxidized by periodate 10 times more rapidly than its isomer. The corresponding ethoxy compounds were prepared and their structures were elucidated in a completely analogous manner. (Author)


Descriptors :   *CYCLOHEXANES , *CYCLOHEXANOLS , SYNTHESIS(CHEMISTRY) , SYNTHESIS(CHEMISTRY) , ORGANIC OXYGEN COMPOUNDS , BROMINE COMPOUNDS , HYDROXIDES , CHEMICAL PROPERTIES , CHEMICAL REACTIONS


Distribution Statement : APPROVED FOR PUBLIC RELEASE