Triethylborane-induced bromine atom-transfer radical addition in aqueous media: Study of the solvent effect on radical addition reactions

H Yorimitsu, H Shinokubo, S Matsubara…

Index: Yorimitsu; Shinokubo; Matsubara; Oshima; Omoto; Fujimoto Journal of Organic Chemistry, 2001 , vol. 66, # 23 p. 7776 - 7785

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Citation Number: 60

Abstract

A mixture of ethyl bromoacetate and 1-octene was treated with triethylborane in water at ambient temperature to provide ethyl 4-bromodecanoate in good yield. The bromine atom- transfer radical addition in benzene was not satisfactory. The addition proceeded smoothly in polar solvents such as DMF and DMSO, protic solvents such as 2, 2, 2-trifluoroethanol and 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol, and aqueous media. Ab initio calculations were ...