Tetrahedron

Organoboranes for synthesis. 1: Protonolysis of trialkylboranes. A convenient non-catalytic conversion of alkenes into saturated compounds via hydroboration- …

HC Brown, KJ Murray

Index: Brown, Herbert C.; Murray, Kenneth J. Tetrahedron, 1986 , vol. 42, # 20 p. 5497 - 5504

Full Text: HTML

Citation Number: 34

Abstract

The protonolysis of trialkylboranes with carboxylic acids proceeds very rapidly for the first group, somewhat slower for the second, but requires elevated temperatures for removal of the third. A close examination of the protonolysis of representative symmetrical, as well as mixed trialkylboranes, reveals that the steric requirements of the alkyl groups attached to boron play an important role in the rate. Secondary alkyl groups protonolyze less readily ...