Monodeoxy-1,4:3,6dianhydrohexitol nitrates with substituent were synthesized , starting from 1,4:3,6&&y 6, 5) or without (6) an additional chloro ohexitol-monoacetates, via 3 as key intermediates. Attempts to generate an unsaturated nitrate ester resulted in a DBN alkylation product (9).