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27.15.1.4.2 Variation 2: Reduction of Conjugated Nitroalkenes

DOI: 10.1055/sos-SD-027-00519

Yamane, M.; Narasaka, K.Science of Synthesis, (200427613.

Conjugated nitroalkenes 17 are converted into oximes 18 by reduction with iron/hydrogen chloride,[‌128‌] titanium(III) chloride,[‌129‌] chromium(II) chloride,[‌130‌‌134‌] zinc/acetic acid,[‌115‌,‌135‌,‌136‌] zinc borohydride,[‌137‌] zinc(II) chloride/hydrogen chloride,[‌138‌] tin(II) chloride,[‌139‌‌143‌] sodium stannite,[‌144‌] lead/acetic acid,[‌145‌] palladium/hydrogen,[‌146‌] palladium on carbon/sodium hypophosphite,[‌147‌] or palladium on carbon/ammonium formate.[‌148‌] Although in most cases the reduction of nitroalkenes is limited to the preparation of ketoximes, aldoximes are synthesized under some mild reaction conditions (Scheme 11).[‌145‌] The major byproducts are ketones or polymeric products. Nitrosoalkenes are intermediates in these reductions of nitroalkenes. Therefore, by combination of the reduction and conjugate addition of nucleophiles to the intermediary nitrosoalkene, varieties of α-substituted oximes such as α-chloro-,[‌138‌] α-hydroxy,[‌132‌,‌133‌] α-alkoxy-,[‌139‌] α-alkylsulfanyl-,[‌139‌] and α-amino oximes[‌138‌,‌143‌] can be prepared. Electroreduction can also be used to prepare oxime derivatives.[‌149‌‌151‌]

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