Mechanism of silver (I) oxide mediated O-alkylation of 2,4-di-O-acyl-myo-inositol 1,3,5-orthoformates: effect of solvent and silver halide on the nature of the intermediates involved

Reaction of 2-O-benzoyl-myo-inositol 1,3,5-orthoformate with alkyl halides in the presence of silver (I) oxide under a variety of conditions have been studied systematically and compared with the corresponding reaction of 2,4-di-O-acyl-myo-inositol 1,3,5-orthoformates. The results indicate that the former is not an intermediate during the alkylation of the latter in DMF. Results obtained on alkylation of the orthoformate esters mentioned above in acetonitrile show that the alkylation of 2-O-benzoyl-myo-inositol 1,3,5-orthoformate which is formed via the transesterification of 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate could be a side reaction. Silver halides, which are generated during alkylation of 2,4-di-O-acyl-myo-inositol 1,3,5-orthoformates, increase their transesterification in DMF.