IPSO-NUCLEOPHILIC VS TELE-NUCLEOPHILIC SUBSTITUTION BY PIPERIDINE ON ISOCOLCHICIDES AND COLCHICIDES BEARING AN ALPHA-LEAVING GROUP

被引：14

作者：

CAVAZZA, M ^{[1
]}

PIETRA, F ^{[1
]}

机构：

[1] UNIV TRENT,IST CHIM,I-38050 TRENT,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 20期

关键词：

D O I：

10.1039/p19950002657

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Product studies of the reactions of piperidine with colchicides carrying a C-10 nucleofugic group show that only ipso substitution occurs. For isocolchicides carrying an X nucleofugic group at C-9, similar behaviour was observed for X = F, OTs or OMe, while for X = SMe, SOMe or Cl tele substitution (at C-ll) competes with ipso substitution. These results together with the observation that the reaction rates for the two series are similar, may be useful in guiding the refunctionalization of similar compounds.

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页码：2657 / 2661

页数：5

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