F. Buckell et al., HYDROLYSIS OF NITRITE ESTERS - PUTATIVE INTERMEDIATES IN THE BIOTRANSFORMATION OF ORGANIC NITRATES, Perkin transactions. 2, (3), 1994, pp. 401-403
Study and comparison of the pH-independent hydrolysis of eight alkyl n
itrites shows 3-nitroso-1,2-glyceryl dinitrate, a putative intermediat
e in the biotransformation of glyceryl trinitrate, to be unexpectedly
reactive and too labile to be detected as a biotransformation intermed
iate in aqueous solution, suggesting a role for neighbouring group par
ticipation by the beta-nitrate group.