Tetrahedron p. 297 - 305 (1987)
Update date:2022-08-04
Topics:
Ohwada, Tomohiko
Ohta, Toshiharu
Shudo, Koichi
β-Nitrostyrenes are diprotonated on the nitro group to yield N,N-dihydroxyiminium-benzyl dications in trifluoromethanesulfonic acid. These dications comprise a new class of reagents that can react with benzene. The reaction is dependent on the substituent (H or alkyl group) at the β-position of nitrostyrene: β-nitrostyrene yields diphenylacetophenoneoxime, and β-methyl-β-nitrostyrene yields acetophenoneoxime and triphenylmethane. An essentially common mechanism is suggested to be involved in both reactions. These reactions are novel examples of acidcatalyzed reactions of nitro olefins.
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