Issue 3, 1978

Reactions of fluoroalkyl radicals generated electrochemically. Part 1. Additions of trifluoromethyl radicals to olefinic and acetylenic bonds

Abstract

Trifluoromethyl radicals, generated by the electrolysis of trifluoroacetic acid in acetonitrile–water–sodium hydroxide reacted with olefins CH2[double bond, length half m-dash]CHX (X = C3H7, C4H9, C5H11, CO2CH3, CN, and CH2CO2CH3) to give a mixture of products of the type CF3CH2CH2X, CF3CH[double bond, length half m-dash]CHX, CF3CH2CH(CF3)X, and (CF3CH2CHX)2. Where X = CO2CH3 trimeric products were also isolated. With hex-1-yne, electrolysis of trifluoroacetic acid gave a mixture of Z- and E-CF3CH[double bond, length half m-dash]CHC4H9 and E-CF3CH[double bond, length half m-dash]C(CF3)C4H9. In contrast cyclopentene produced only cyclopentyl trifluoroacetates.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 202-209

Reactions of fluoroalkyl radicals generated electrochemically. Part 1. Additions of trifluoromethyl radicals to olefinic and acetylenic bonds

C. J. Brookes, P. L. Coe, A. E. Pedler and J. C. Tatlow, J. Chem. Soc., Perkin Trans. 1, 1978, 202 DOI: 10.1039/P19780000202

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