The reduction of 2-nitrocyclohexanones to the 2-nitrocyclohexanols with sodium borohydride followed by treatment of the ,9-nitroalcohols with sodium hydride and subsequent acidification of the salts leads to the regioselective synthesis of conjugated nitrocyclohexenes from cyclohexanones. The resurgent interest in the chemistry of aliphatic nitrocompounds is evidenced by the recent reviews about such compounds.2 l-Nitrocycloalkenes2'a'b,c,3 are one of the most useful types of aliphatic nitro compounds. There are three recent reports of new methods for the synthesis of 1-nitroalkenes: 1) the base catalyzed elimination of HHgCl from nitromercurials prepared by the nitromercuration of olefins3a, 2) the replacement of tin by a nitro group in vinyl stannanes prepared from tosylhydrazones of cycloalkanones 3b and 3) the oxidative elimination of C5H5SeOH from a-nitro(phenylseleno)alkanes prepared from nitroalkanes and phenylselenyl bromide3c. These methods are particularly suitable for the preparation of cyclic nitroalkenes. The classical method4 of the elimination of water from B-nitroalcohols formed by the condensation of aldehydes and ketones with nitroalkanes (Henry reaction) is limited primarily to the synthesis of acyclic 1-nitroalkenes because of the inaccessibility of the acyclic nitro carbonyl compounds necessary for the condensation reaction to produce the cyclic B-nitroalcohols. However, if an alternate synthesis were available, B-nitroalcohols would serve as ideal precursors for the synthesis of conjugated nitrocycloalkenes. We have recently reported the synthesis of a-nitrocyclopentanones 596 and a-nitrocyclohexanones1*7 by the nitration of ketone enol acetates with nitric acid. We now wish to report the chemoselective reduction of these a-nitroketones to the B-nitrocyclo-. : alkanols followed by dehydration as a method of synthesis of conjugated nitrocycloalkenes from cycloalkanones.