IRON(III) MEDIATED TRANSFORMATIONS OF CYCLOPROPYLTRIMETHYLSILYL ETHERS .1. FREE-RADICAL TANDEM RING EXPANSION-CYCLIZATION REACTIONS FOR THE RAPID CONSTRUCTION OF [N30] BICYCLIC RING-SYSTEMS

被引:51
作者
BOOKERMILBURN, KI [1 ]
THOMPSON, DF [1 ]
机构
[1] UNIV SALFORD,DEPT CHEM,SALFORD M5 4WT,LANCS,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 18期
关键词
D O I
10.1039/p19950002315
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of a number of [n.1.0] cyclopropyl trimethylsilyl ethers with anhydrous ferric chloride in dry dimethylformamide leads to diastereoisomerically pure [n.3.0] bicyclic chloro ketones by a novel tandem ring expansion-cyclisation sequence. The reaction is thought to proceed by a mechanism involving the intermediacy of a cyclopropyl alkoxy radical.
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页码:2315 / 2321
页数:7
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