Preparation of Nitroalkenes: Substitution Reaction via Addition-Elimination Using β-Nitrovinyl Sulfoxides

Manabu Node; Akichika Itoh; Kiyoharu Nishide; Hitoshi Abe; Takeo Kawabata; Yukio Masaki; Kaoru Fuji

doi:10.1055/s-1992-26318

Synthesis 1992; 1992(11): 1119-1124
DOI: 10.1055/s-1992-26318

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Preparation of Nitroalkenes: Substitution Reaction via Addition-Elimination Using β-Nitrovinyl Sulfoxides

Manabu Node^* , Akichika Itoh, Kiyoharu Nishide, Hitoshi Abe, Takeo Kawabata, Yukio Masaki, Kaoru Fuji

^*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan

Abstract

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Nitroalkenes were prepared by the substitution reaction of β-nitro-vinyl sulfides and sulfoxides [1-ethylsulfinyl-2-nitrocyclohex-1-ene, -cyclohept-1-ene, and (E)-2-ethylsulfinyl-1-nitroprop-1-ene] with a variety of carbon nucleophiles (i. e. alkylmetal reagents and enolates of carbonyl compounds), via an addition-elimination sequence. The sulfoxide as a leaving group was suitable for the reaction with an enolate of carbonyl compounds. This method was useful for the synthesis of nitroalkenes [2-nitrocyclohex-1-enyl(hept-1-enyl)- and 2-nitro-1-methylvinyl-substituted cyclohexanone, γ-butyrolactones, δ-valerolactones, 2-pyrrolidinones and piperidinones].

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