ADDITIONS OF CUCN-DERIVED STANNYLCUPRATES TO TERMINAL ALKYNES - A COMPARATIVE SPECTROSCOPIC AND CHEMICAL STUDY

被引：39

作者：

SINGER, RD ^{[1
]}

HUTZINGER, MW ^{[1
]}

OEHLSCHLAGER, AC ^{[1
]}

机构：

[1] SIMON FRASER UNIV,DEPT CHEM,BURNABY V5A 1S6,BC,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 16期

关键词：

D O I：

10.1021/jo00016a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stannylcupration of terminal alkynes 4a,b with cuprates 1-3 proceeds rapidly and reversibly above -35-degrees-C to afford vinylcuprate intermediates 5a,b and 6a,b. These intermediates have been characterized by H-2 and C-13 NMR labeling experiments. Corroborating evidence for this reversible addition comes from further chemical tests and cross-over experiments that show the thermodynamic favorability of the adducts. Further comparative study of reaction products and byproducts shows 2 to be the stannylcuprate of choice for the preparation of vinylstannanes from terminal alkynes.

引用

页码：4933 / 4938

页数：6

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