The transformation of gem-dihalocyclopropanes (1) into 1-alkyl-1-butylcyclopropanes (2 and 3) is established by successive treatment with dibutylcopperlithium and several electrophiles. This sequence is found to be stereochemically controllable and is successfully applied to dl-sirenin synthesis. In contrast to the reaction of dibutylcopperlithium, dimethyl- and divinylcopperlithiums convert 1,1-dibromo-2-phenylcyclopropane (1a) into 1-bromo-1-methyl- and 1-bromo-1-vinyl-2-phenylcyclopropanes (15a, 16a and 15b, 16b) respectively.
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Kitatani et al. (1977) studied this question.
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