THE REACTION OF GEMINAL BROMONITROALKANES WITH NUCLEOPHILES .1. THE DECOMPOSITION OF 2-BROMO-2-NITROPROPANE-1,3-DIOL (BRONOPOL) IN AQUEOUS BASE

2-Bromo-2-nitropropane-1,3-diol decomposes in aqueous base to give tris(hydroxymethyl)nitromethane, glycolic acid, formic acid, methanol and 2,2-dinitroethanol. It also releases NO2- and Br- ions but not BrO-. These products are shown to form via four concurrent decomposition pathways, three of which involve 2-bromo-2-nitroethanol as a reactive intermediate.