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Reactions of Tricyclo[4.1.0.0 2,7 ]heptane and 1-Methyltricyclo[4.1.0.0 2,7 ]heptane with 2-Bromoethanesulfonyl Bromide
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-07-20 , DOI: 10.1134/s1070428020060081 S. G. Kostryukov , Yu. Yu. Masterova
中文翻译:
三环[4.1.0.0 2,7]庚烷和1-甲基三环[4.1.0.0 2,7]庚烷与2-溴乙烷磺酰基溴的反应
更新日期:2020-07-20
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-07-20 , DOI: 10.1134/s1070428020060081 S. G. Kostryukov , Yu. Yu. Masterova
Abstract
2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.02,7]heptane and 1-methyltricyclo[4.1.0.02,7]heptane according to a radical mechanism to give products of both anti and syn addition across the C1–C7 central bicyclobutane bond having a norpinane (bicyclo[3.1.1]heptane) structure. Treatment of the adducts with triethylamine leads to the formation of vinyl sulfones as a result of 1,2-dehydrobromination, and their reaction with sodium methoxide involves 1,2- and 1,3-dehydrobromination and nucleophilic addition, depending on the substrate structure and reactant ratio.中文翻译:
三环[4.1.0.0 2,7]庚烷和1-甲基三环[4.1.0.0 2,7]庚烷与2-溴乙烷磺酰基溴的反应