The Experts below are selected from a list of 93 Experts worldwide ranked by ideXlab platform

Qilong Shen - One of the best experts on this subject based on the ideXlab platform.

Feng Shen - One of the best experts on this subject based on the ideXlab platform.

Panpan Zhang - One of the best experts on this subject based on the ideXlab platform.

Nagatoshi Nishiwaki - One of the best experts on this subject based on the ideXlab platform.

  • alkynylation and cyanation of alkenes using diverse properties of a nitro Group
    Journal of Organic Chemistry, 2018
    Co-Authors: Haruyasu Asahara, Ayano Sofue, Yasuyuki Kuroda, Nagatoshi Nishiwaki
    Abstract:

    In the work being reported here, β-nitrostyrenes bearing an Ethoxycarbonyl Group at the β-position serve as scaffolds for the synthesis of α,β-difunctionalized alkenes. Nitrocinnamates undergo Michael addition reactions with versatile sp3- and sp2-nucleophiles such as alcohols, Grignard reagents, alkylcopper, and dialkylzinc to afford β-substituted nitroethane derivatives. However, various attempts to obtain a double bond via nitrous acid elimination failed because steric repulsion between the newly introduced sp3/sp2 substituent and the nitro Group hampered the required anti-coplanar conformation. This problem was successfully overcome using a smaller sp-nucleophile such as lithium acetylide, potassium cyanide, or trimethylsilyl cyanide. While treatment of the adduct with a strong base did not lead to the elimination of nitrous acid, the weaker triethylamine efficiently afforded functionalized enynes and acrylonitriles in high yields.

  • Alkynylation and Cyanation of Alkenes Using Diverse Properties of a Nitro Group
    2018
    Co-Authors: Haruyasu Asahara, Ayano Sofue, Yasuyuki Kuroda, Nagatoshi Nishiwaki
    Abstract:

    In the work being reported here, β-nitrostyrenes bearing an Ethoxycarbonyl Group at the β-position serve as scaffolds for the synthesis of α,β-difunctionalized alkenes. Nitrocinnamates undergo Michael addition reactions with versatile sp3- and sp2-nucleophiles such as alcohols, Grignard reagents, alkylcopper, and dialkylzinc to afford β-substituted nitroethane derivatives. However, various attempts to obtain a double bond via nitrous acid elimination failed because steric repulsion between the newly introduced sp3/sp2 substituent and the nitro Group hampered the required anti-coplanar conformation. This problem was successfully overcome using a smaller sp-nucleophile such as lithium acetylide, potassium cyanide, or trimethylsilyl cyanide. While treatment of the adduct with a strong base did not lead to the elimination of nitrous acid, the weaker triethylamine efficiently afforded functionalized enynes and acrylonitriles in high yields

Susung Oh - One of the best experts on this subject based on the ideXlab platform.