The Journal of Organic Chemistry

Vinylic organoboranes. 3. Pheromones via organoboranes. 1. Stereospecific synthesis of straight-chain (Z)-monoolefinic insect pheromones via lithium (1-alkynyl) …

HC Brown, KK Wang

Index: Brown, Herbert C.; Wang, Kung K. Journal of Organic Chemistry, 1986 , vol. 51, # 24 p. 4514 - 4517

Full Text: HTML

Citation Number: 18

Abstract

Conclusions It has been determined that a number of alkenyldialkylboranes can be protonolyzed cleanly in high yields utilizing only methanol as the protonolyzing reagent. In those cases where steric hindrance slows the protonolysis, a catalytic amount (1 mol%) of pivalic acid appears to be most effective in bringing about efficient protonolysis. Thus the hydroboration-protonolysis procedure promises to be the method of choice for the efficient ...