TfOH promoted reactions of vinyl gem- dichlorocyclopropanes with arenes: access to aryl gem -dichloropentenes
作者:Anna A. Kazakova、Anna A. Bogomazova、Roman O. Iakovenko、Simon S. Zlotsky、Aleksander V. Vasilyev
DOI:10.1016/j.tetlet.2016.08.008
日期:2016.9
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
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,生成1,1-二氯-2-甲基-4-芳基戊-1-烯(产率30-68%)。