Reaction of alkenylboranes with methylcopper. A convenient new procedure for the synthesis of symmetrical (E, E)-1, 3-dienes

Y Yamamoto, H Yatagai, K Maruyama…

Index: Yamamoto,Y. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 5652 - 5656

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Citation Number: 39

Abstract

Abstract: Dialkenylchloroboranes (5), readily available through the reaction of acetylenes with chloroborane-ethyl etherate, react with 3 molar equiv of methylcopper to produce symmetrical (E, E)-1, 3-dienes (6) in high yields. The stereochemical pu-rity of the product is> 99%. The similar reaction with alkenyldisiamylboranes or alkenyldicyclohexylboranes produces (E, E)-1, 3-dienes in moderate yields along with a considerable amount of by- ...

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