Cyanocarbon Chemistry. XIX.1,2 Tetracyanocyclobutanes from Tetracyanoethylene and Electron-rich Alkenes
Cyanocarbon Chemistry. XIX.1,2 Tetracyanocyclobutanes from Tetracyanoethylene and Electron-rich Alkenes
复制标题
氰碳化学。
DOI：
10.1021/ja00870a037
复制
发表时间：
1962
影响因子：
15
通讯作者：
B. Mckusick
中科院分区：
文献类型：
--
作者：
J. K. Williams;D. Wiley;B. Mckusick
在过去几年中，外族化合物、氟代烯烃和烯酮与烯烃热加成生成环丁烷已得到广泛研究，目前是生成环丁烷的最重要途径之一，其中一些环丁烷可用作脂环族化合物的前体。 3· 4 四氰乙烯是第尔斯-阿尔德反应中的反应性亲二烯体，5 已被观察到与一些1, 3-二烯体系形成环丁烷衍生物，而第尔斯-阿尔德加成很难或不可能。 6 现在发现四氰乙烯很容易与多种富电子烯烃形成1,1,2,2-四氰基环丁烷(I)。 7 三氰基乙烯的行为类似。正如后续论文中将描述的，这些多氰基环丁烷是 1,1,2-三氰基丁二烯和
The thermal addition of alienes, fluoroalkenes and ketenes to alkenes to give cyclobutanes has been extensively investigated in the last few years and is now one of the most important routes to cyclobutanes, some of which are useful as pre-cursors of alicyclic compounds. 3· 4 Tetracyanoethylene, a reactive dienophile in the Diels-Alder reaction, 5 has been observed to form cyclobutane derivatives with a few 1, 3-diene systemsto which Diels-Alder addition is difficult or impossible. 6 It has now been found that tetracyanoethylene readily forms 1, 1, 2, 2-tetracyanocyclobutanes (I) with a variety of electron-rich alkenes. 7 Tricyano-ethylene behaves similarly. As will be described in a subsequent paper, these polycyanocyclobutanes are good sources of 1, 1, 2-tricyanobutadienes and