106185-57-3Relevant academic research and scientific papers
Regioselective Preparation of Cyclohexadienes or Aromatic Nitro Compounds by Diels-Alder Reactions of β-Sulfonylnitroolefins or β-Sulfinylnitroethylene
Ono, Noboru,Kamimura, Akio,Kaji, Aritsune
, p. 251 - 258 (2007/10/02)
β-Sulfonylnitroolefins react with various dienes to give 4-nitro-5-(phenylsulfonyl)cyclohexenes under mild conditions, where the nitro group controls the direction of the addition more effectively than the sulfonyl group.Subsequent treatment of the adducts with Bu3SnH results in the reductive elimination of the nitro and sulfonyl groups to give 1,4-cyclohexadienes.The Diels-Alder reaction of β-sulfinylnitroethylene with dienes and subsequent thermal elimination of sulfenic acid give 1-nitro-1,4-cyclohexadienes, which are readily aromatized to give nitrobenzene derivatives.Thus, β-sulfonylnitroolefins or β-sulfinylnitroethylene is regarded as alkynes or nitroacetylene equivalents for the Diels-Alder reaction, respectively.
β-SULFONYLNITROOLEFINS AS VERY REACTIVE ALKYNE-EQUIVALENTS IN DIELS-ALDER REACTIONS
Ono, Noboru,Kamimura, Akio,Kaji, Aritsune
, p. 1595 - 1598 (2007/10/02)
Very reactive dienophiles, β-sulfonylnitroolefins, are prepared starting from β-nitro alcohols.The high activation due to the nitro and the sulfonyl groups promotes the Diels-Alder reaction to various dienes under mild conditions.Reductive elimination of
