MICHAEL REACTIONS OF ASCORBIC-ACID .4. NITROSTYRENE AS A MICHAEL ACCEPTOR TOWARD VITAMIN-C

The nitrostyrene derivatives 1a-m, prepared by the reaction of nitrome thane with the appropriate substituted benzaldehyde, were reacted with ascorbic acid in a Michael type reaction to the new compounds 2a-h. T he structural assignment of the resulting mixture of diastereomers cou ld be performed by means of two dimensional homo- and heterocorrelated NMR spectroscopy and comparison to known Michael adducts of ascorbic acid. Catalytic hydrogenolysis of 2a yielded the rearranged compound 7 , formed by intramolecular aminolysis in analogy to the rearrangement of the Michael adduct of ascorbic acid and methylvinylketone 3 given i n the literature. On testing, the C-nucleoside 7 did not reveal virost atic or cytostatic effects.