顺式-2-烯-4-炔-1-酮的呋喃形成反应。

Furan forming reactions of cis-2-alken-4-yn-1-ones.

作者信息

Casey Charles P, Strotman Neil A

机构信息

Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.

出版信息

J Org Chem. 2005 Apr 1;70(7):2576-81. doi: 10.1021/jo047762n.

DOI:10.1021/jo047762n

PMID:15787545

Abstract

[reactions: see text] The cis-2-alken-4-yn-1-one, 1-phenyl-cis-2-penten-4-yn-1-one (cis-1), readily dimerizes on treatment with weak acid to give the 1,2-difurylethylenes, trans- and cis-1,2 di(2-(5-phenylfuryl))ethene (trans-1 and cis-2), in 62% and 23% yields, respectively. Trimerization of cis-1 to trans,trans-1,2,3-tri(2-(5-phenylfuryl)cyclopropane (4) occurred as a byproduct of treatment with weak acid. These reactions demonstrate the 2-furylcarbenoid reactivity of cis-2-alken-4-yn-1-ones.

摘要

[反应：见正文] 顺式-2-烯-4-炔-1-酮，1-苯基-顺式-2-戊烯-4-炔-1-酮（顺式-1），用弱酸处理时容易二聚，分别以62%和23%的产率生成1,2-二呋喃乙烯，反式和顺式-1,2-二（2-（5-苯基呋喃基））乙烯（反式-1和顺式-2）。顺式-1三聚生成反式，反式-1,2,3-三（2-（5-苯基呋喃基））环丙烷（4）是用弱酸处理的副产物。这些反应证明了顺式-2-烯-4-炔-1-酮的2-呋喃基类卡宾反应活性。