BUILDING-BLOCKS FOR CASCADE POLYMERS .3. FACILE ELIMINATION OF NITROUS-ACID FROM QUATERNARY NITROALKANES

The recent resurgence of the chemistry of nitroalkanes has largely dealt with their reactivity toward nucleophiles;2 in particular, the new synthetic approaches have utilized the single-electron-transfer (SET) mechanism.3 Attention has also been devoted to SRN1 reactions of nucleophiles with a-substituted nitroalkanes; however, with excess base, nitroalkanes eliminated HNO2 to afford the corresponding α,β-unsaturated derivatives. Recently, facile elimination of HNO2 from an angular tertiary nitro group upon contact with silica gel or neutral alumina at ambient temperature has been reported.4. © 1990, American Chemical Society. All rights reserved.