Mono-and bis(5-O-nitro-1,4:3,6-dianhydro-D-sorbit-2-yl) phosphates: Synthesis and reactions with hydroxy-and amino-containing compounds

Article abstract of DOI:10.1007/s11172-007-0327-2

The reaction of 1,4:3,6-dianhydro-D-sorbitol 5-nitrate with POCl ₃ afforded mono-and bis(5-O-nitro-1,4:3,6-dianhydro-D-sorbit-2-yl) phosphorochloridates, whose hydrolysis resulted in phosphoric acid mono-and diesters. The subsequent treatment of these compounds with bases gave sodium and cyclohexylammonium salts. The reactions of phosphorochloridates with phenol, pentaerythritol dibromohydrin, and ethylenimine in the presence of organic bases afford mixed phosphates and phosphoramidates.