Novel silicon-promoted cycloalkylation of alkenylmetal derivatives

E Negishi, LD Boardman, JM Tour…

Index: Negishi, Ei-ichi; Boardman, Larry D.; Tour, James M.; Sawada, Hiroyuki; Rand, Cynthia L. Journal of the American Chemical Society, 1983 , vol. 105, # 20 p. 6344 - 6346

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Citation Number: 66

Abstract

E and Z mixture in 80-90% yield. As expected, its treatment with AlC13 (1.1 equiv) in CH2C12 at 0" C produces 5 in 84% yield, indicating that hydrometalation or carbometalation products can be intermediates for the cyclic products. It is also worth noting that there is no detectable reaction between 9 and homoallyl bromide. Finally, the intermediacy of cyclopropylcarbinyl derivatives is supported by the reaction of 10 with DIBAH in pentane ...