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TfOH promoted reactions of vinyl gem-dichlorocyclopropanes with arenes: access to aryl gem-dichloropentenes
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2016-08-31 00:59:24
Anna A. Kazakova, Anna A. Bogomazova, Roman O. Iakovenko, Simon S. Zlotsky, Aleksander V. Vasilyev

The reaction of 1,1-dichloro-2-vinylcyclopropane with arenes under the action of the superacid TfOH afforded 3-aryl-1,1-dichloropent-1-enes (25–43% yield), as the products of cyclopropane ring opening. The reaction of 1,1-dichloro-2-methyl-2-vinylcyclopropane was realized as a two-step procedure, including initial in situ generation of the corresponding triflate, 5,5-dichloro-4-methylpent-4-en-2-yl trifluoromethanesulfonate, from the cyclopropane and TfOH, followed by reaction with arenes and TfOH to give 1,1-dichloro-2-methyl-4-arylpent-1-enes (30–68% yield).

中文翻译:

TfOH促进乙烯基宝石-二氯环丙烷与芳烃的反应:获得芳基宝石-二氯戊烯

1,1-二氯-2-乙烯基环丙烷在超强酸TfOH作用下与芳烃反应,生成3-芳基-1,1-二氯戊-1-烯(收率25-43%),为环丙烷开环产物。1,1-二氯-2-甲基-2-乙烯基环丙烷的反应分两个步骤进行,包括初始原位生成相应的三氟甲磺酸盐,5,5-二氯-4-甲基戊-4-烯-2环丙烷和TfOH中的三氟甲磺酸正丁基酯,然后与芳烃和TfOH反应,得到1,1-二氯-2-甲基-4-芳基戊-1-烯(30-68%收率)。
更新日期:2016-08-31
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