Abstract: This application relates to 3-substituted and 4-substituted cis-diols. Specifically, there are provided 3-substituted diols of formula (II) and 4-substituted cis-diols having (1S, 2R) and (1R, 2S) absolute configurations of formulae (III) and (IV). Also provided are processes For making such 3- and 4-substituted cis-diols using a reductive fission reaction. The compounds described herein are useful as synthons for the preparation of various compounds including therapeutics, agricultural, polymers and other classes of compounds. In formulae (II, III and IV), R is halogen, CN, aryl alkyl, alkenyl alkynyl O-alkyl, CF.sub.3 or NO.sub.2.

Abstract: Described herein is a process for the preparation of (1S,2R)-1,2-epoxy-1,2,3,4-tetrahydronaphthalene having the Formula (I): ##STR1## which comprises the steps of (a) hydrogenating the compound of Formula (II) to form cis-(1R, 2S)-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene having the Formula (V): ##STR2## (b) reacting the dihydroxy compound of Formula (V) with a sulphonyl halide of formula R.sup.1 SO.sub.2 Z wherein R.sup.1 is methyl, ethyl, trifluoromethyl, phenyl or p-tolyl, and Z is fluorine, chlorine, bromine or iodine to give a bis-sulphonyl ester of formula (X): ##STR3## and (c) treating the bis-sulphonyl ester (X) with an alkali metal carbonate or alkali metal hydroxide to give the compound of Formula (I).