Bulletin of the Chemical Society of Japan

Oxygen-accelerated generation of the bromocarbenoid reagent of zinc from diethylzinc and bromoform. Bromocyclopropanes from olefins.

S Miyano, H Hashimoto

Index: Miyano,S.; Hashimoto,H. Bulletin of the Chemical Society of Japan, 1975 , vol. 48, p. 3665 - 3668

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Citation Number: 10

Abstract

Oxygen greatly accelerates the generation of the bromocarbenoid reagent of zinc from diethylzinc and bromoform. Olefins, including cyclohexene, cyclooctene, 1-hexene, cis-and trans-2-butene, isobutene, and 2-methyl-2-butene were bromocyclopropanated in yields of ca. 60–85% using a diethylzinc-bromoform-oxygen system. The bromocarbenoid showed high syn-selectivity for the addition to cyclooctene and cis-2-butene. 9-Bromo-9-deutero [ ...