Vinylic organoboranes. 4. A general, one-pot synthesis of 6-and 7-alkyn-1-ols via boracyclanes. Influence of steric effects in the iodination of lithium alkynyl ate …

HC Brown, D Basavaiah, NG Bhat

Index: Brown, Herbert C.; Basavaiah, D.; Bhat, N. G. Journal of Organic Chemistry, 1986 , vol. 51, # 24 p. 4518 - 4521

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Citation Number: 14

Abstract

The iodination of the “ate” complexes derived from various B-alkoxyborinane derivatives and 1-alkynyllithium has been investigated. The results indicate the ate complex from B- methoxyborinane is converted into the desired 6-alkyn-1-01 in a yield of only 22%, with much larger amounts, 65%, of the undesired I-iodo-1-alkyne. Increases in the steric bulk of the alkoxy group on boron increase the yield of the required 6-alkyn-1-01 with the best ...