NUCLEOPHILIC DISPLACEMENT REACTIONS OF THE METHANESULFONATES OF THE 1-O-BENZOYL-1,2-, -1,3-, AND -1,4-GLYCOLS

Article abstract of DOI:10.1016/S0040-4039(00)88309-4

Nucleophilic displacement reactions of the methanesulfonates (8a-c) of the 1-O-benzoyl-1,2-, -1,3-, and -1,4-glycols (7a-c) with potassium acetate in boiling acetic anhydride have been examined.Both benzoyloxy-group participation pathway (path A) and S_N2 displacement pathway (path B) have been involved in the 1,2-(8a)- and 1,3-(8b)-substrates to give a mixture of the primary (10a,b) and the secondary (11a,b) acetates with complete inversion of chiralities.On the other hand, only S_N2 displacement pathway (path B) has been involved in the 1,4-substrate (8c) to give the secondary acetate (11c) with inversion of the chirality.