Controlled reaction of oxygen with alkyldichloroborane etherates. Synthesis of alkyl hydroperoxides in high yield

MM Midland, HC Brown

Index: Midland, M. M.; Brown, H. C. Journal of the American Chemical Society, 1973 , vol. 95, p. 4069 - 4070

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Citation Number: 21

Abstract

Alkyldichloroboranes in inert solvents react remarkably rapidly with 0.5 molar equiv of oxygen, either at 0 or-78". The reaction is strongly inhibited by iodine and must involve a free- radical chain process, yet the product contains little peroxide. In diethyl ether the reaction proceeds readily with the uptake of 1 molar equiv of oxygen. The product is readily hydrolyzed to the corresponding alkyl hydroperoxide. This procedure provides a ...