Synthesis, Structure, and E− Z Isomerization of β-(Hetero) aryl-α-nitro-α, β-enals

…, L Ozores-Viturro, M Fernández-González…

Index: Martinez-Bescos, Patricia; Cagide-Fagin, Fernando; Roa, Luis F.; Ortiz-Lara, Juan Carlos; Kierus, Krzysztof; Ozores-Viturro, Lidia; Fernandez-Gonzalez, Marta; Alonso, Ricardo Journal of Organic Chemistry, 2008 , vol. 73, # 10 p. 3745 - 3753

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Citation Number: 17

Abstract

The first general methodology for the gram-scale preparation of previously overlooked β- (hetero) aryl-α-nitro-α, β-enals (3) is reported. Condensation of (hetero) aromatic aldehydes with 2-nitroethanol gave the E-isomers of uncommon β-(hetero) aryl-α-hydroxymethyl-α, β- unsatured-nitroalkenes (2), as determined by NOE and X-ray studies. α-Nitro-α, β-enals 3 were subsequently obtained by hypervalent iodine oxidation of 2 as E− Z-mixtures in solid ...