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The alkaline detosylation of 4-tosyl-D-man-nosan/3 has been shown to proceed with Walden inversion and cis ethylene oxide ring formation to yield an anhydro derivative which is presumably 3,4-anhydro-D-talosan< 1,5>/3<1,6>. The anhydro compound, upon treatment with an acid acetylating mixture, yields a mixture of D-mannose and D-idose pentaacetates. The hexoses present have been identified by conversion of the acetates to characteristic hexitol hexaacetates. The reactions outlined are in agreement with other reactions in the carbohydrate series involving Walden inversions with ethylene oxide ring formation and rupture, as studied especially by Robertson and his colleagues, and the present results justify the conclusion that the structure and the configuration of the anhydro compound are those of 3,4-anhydro-D-talosan-d.d-and L-iditol hexaacetates form a crystalline racemate which melts much higher than the components and differs from them in crystallographic optical properties. Bethesda, Md.

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