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Communication | Special issue | Vol 15, No. 1, 1981, pp.231-236
Published online, 1st January, 1970
DOI: 10.3987/S-1981-01-0231
Reaction of B-(1-Alkenyl)-dialkyboranes with Isocyanates

Bakthan Singaram, Gary A. Molander and Herbert C. Brown*

*Wetherill Laboratory, Purdue University, West Lafayette, Indiana 47907, U.S.A.

Abstract

9-(1-Alkenyl )-9-borabicyclo[3.3.1]nonanes [9-(1-alkenyl)-9-BBN], easily prepared by hydroboration of the corresponding alkynes with 9-borabicyclo[3.3.1]nonane (9-BBN), undergo remarkably facile reaction with two equivalents of isocyanates to give the intermediates (6), which on hydrolysis, provide in excellent yield N,N’-disubstituted N-(2-alkenoyl)-ureas. B-(1-Octenyl)-dicyclohexylborane reacts with aliphatic and aromatic isocyanates to furnish the novel heterocycle (11), which on hydrolysis yields N,N’-disubstituted N-(3-cyclohexylnonanyl)-ureas. B-(1-Alkenyl)disiamylboranes are inert towards isocyanates.