Abstract
Several transformations starting from trans, trans-2-nitrocyclohexane-1,3-diol (1) and its diacetate (2) were carried out as model reactions for synthetic work on nitro sugars. They included methylation with diazomethane, dehydration, dehydroacetylation, nucleophilic elimination–additions with alcohols, and bromination. The monomethyl ether of 1 (3), the monomethyl ether acetate (5), the dimethyl and dibenzyl ethers (4 and 9), bromonitro compounds derived from 1 and 4 (13 and 14), and four 3-substituted 2-nitro-cyclohexenes with methoxyl, ethoxyl, acetoxyl, and hydroxyl groups as substituents (6, 8, 7, and 11, respectively) were obtained in these studies. The nitronate formation of 1 and 4 and attendant production of nitroolefins was investigated by u.v. spectroscopy.
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