SYNTHESIS OF ALLYSTANNANES AND VINYLSTANNANES BY THE STANNYL-CUPRATION OF ALLENES

被引：33

作者：

BARBERO, A

CUADRADO, P

FLEMING, I

GONZALEZ, AM

PULIDO, FJ

机构：

[1] UNIV VALLADOLID,DEPT QUIM ORGAN,E-47011 VALLADOLID,SPAIN

[2] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 03期

关键词：

D O I：

10.1039/p19920000327

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stannyl-cupration of allenes followed by electrophilic attack gives allyl-and vinyl-stannanes with a variety of substitution patterns. The regiochemistry of the reaction depends upon the temperature at which the intermediate cuprate is quenched with an electrophile. With allene itself, the allylstannane-vinylcuprate 1-(tributylstannylmethyl)vinylcuprate, 5, is the product of kinetically controlled addition, but the vinylstannane-allylcuprate 2-(tributylstannyl)allylcuprate, 6, is thermodynamically lower in energy. The equilibration between these isomers begins to take place between -100 and -78-degrees-C.

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页码：327 / 331

页数：5

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