TRANS-ANNULAR CYCLIZATIONS OF 1-AZA-4-CYCLOOCTENE

被引:55
作者
WILSON, SR
SAWICKI, RA
机构
[1] Department of Chemistry, Indiana University, Indiana
关键词
D O I
10.1021/jo01316a027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereospecific, transannular cyclizations of l-aza-4-cyclooctene (1) are described. Compound 1 reacts with electrophiles (Br2 I2, HgCl2 PhSBr, PhSeBr) to produce 1-substituted pyrrolizidines 6. The stereochemistry of the bromine-induced cyclization was determined by X-ray crystallography. The reaction proceeds via transannular reaction of the nitrogen with the corresponding “onium” ion. There is no evidence of through-space (transannular) interaction of the amine and the double bond by PES. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:287 / 291
页数:5
相关论文
共 36 条