ORGANOBORANES .54. EXPLORATION OF THE REACTIONS OF (ALPHA-HALOALLYL)LITHIUM WITH ORGANOBORANE DERIVATIVES - SIMPLE AND CONVENIENT PROCEDURE FOR THE SYNTHESIS OF 3-CARBON HOMOLOGATED BORONATE ESTERS AND TERMINAL ALKENES

被引:27
作者
BROWN, HC
RANGAISHENVI, MV
JAYARAMAN, S
机构
[1] H. C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana 47907
关键词
D O I
10.1021/om00041a029
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthetic utility of (alpha-haloallyl)lithium generated in situ for the facile transfer reaction of various organoborane derivatives, such as R3B, R2BOR', and RB(OR')2, has been explored. This has led to the synthesis of alpha-vinylboronate esters, RCH(CH=CH2)B(OR')2, which are readily isomerized thermally to the corresponding allylboronate esters with the boron atom on the less substituted carbon atom, RCH=CHCH2B(OR')2. Catalytic hydrogenation of these allylboronate esters furnishes saturated boronate esters, RCH2CH2CH2B(OR')2, providing a three-carbon homologation of the original R-B < moiety. Protonolysis in place of hydrogenation affords the corresponding terminal alkenes RCH2CH=CH2.
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页码:1948 / 1954
页数:7
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