Rearrangement Reactions of 1,1-Divinyl-2-phenylcyclopropanes

被引：14
作者：
Ben Hay, E. [1 ]
Zhang, Hanmo [1 ]
Curran, Dennis P. [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 01期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
VINYLCYCLOPENTANE SYNTHESIS; COPE REARRANGEMENT; VINYLCYCLOPROPANES; (+/-)-MELOSCINE; 1,1-DIVINYLCYCLOPROPANE; DIVINYLCYCLOPROPANE; (+/-)-EPIMELOSCINE; CYCLOPROPANES; DERIVATIVES; MELOSCINE;
D O I：
10.1021/ja510608u
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
1,1-Divinyl-2-phenylcyclopropanes are entry points to a rich area of rearrangement chemistry. With N,N-diallyl amide substrates, tandem radical cyclizations can be initiated at room temperature. Warming provides products of pure thermal rearrangements with acids, ester, and amides. These isomerizations give vinylcyclopentenes resulting from divinylcyclopropane rearrangements and more deeply rearranged tricyclic spirolactams resulting from aromatic Cope rearrangements followed by ene reactions. Conversion of the carbonyl group to an alcohol or ether opens retro-ene pathways followed by either tautomerization or Claisen rearrangement.
引用
收藏
页码：322 / 327
页数：6
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