REACTION OF BIS(2-OXOCYCLOHEXYL)METHANE WITH HYDROGEN SELENIDE

Bis (2-oxocyclohexyl) methane reacts with hydrogen selenide in polar solvents without a catalyst to give a product of nucleophilic addition of hydrogen selenide at one of the carbonyl groups, which exists in the form of three equilibrium forms, viz., 2-hemolselenolcyclohexyl-2-cyclohexanonylmethane, perhydroselenoxanthene-11,13-diol, and perhydro-11-xanthenol-13-selenol. The latter under the influence of an alcohol solution of alkali form 2,3-tetramethylenebicyclo[3.3.1]nonanon-9-ol, with hydrogen chloride; they react with hydrogen chloride to give sym-octahydroselenoxanthene, and trifluoroacetic acid converts them to a mixture of sym-octa-hydroselenoxanthylium trifluoroacetate and perhydroselenoxanthene. The trifluoroacetate reacts with perchloric acid to give sym-octahydroselenoxanthylium perchlorate.