Fused thiirene sulfoxides. Synthesis via [2 + 4] cycloaddition of thiiranoradialene sulfoxide and structural characterization
Fused thiirene sulfoxides. Synthesis via [2 + 4] cycloaddition of thiiranoradialene sulfoxide and structural characterization
复制标题
稠合的硫杂环丙亚砜。
DOI：
10.1021/ja00382a056
复制
发表时间：
1982
期刊：
影响因子：
--
通讯作者：
K. Ueno
中科院分区：
文献类型：
--
作者：
W. Andō;Y. Hanyu;T. Takata;K. Ueno
注意力集中在轴烯与亲二烯体的[2+ 4]环加成上，[3]轴烯2及其类似物的实例是未知的。该加成在合成上可用作将双键引入与六元环稠合的三元环中的手段，从而得到高度应变的化合物（eq 1）。1和2可以被视为潜在的前体，用于合成六元环稠合到硫杂环和硫杂环亚砜单元，分别。本文首次报道了由硫杂环戊二烯亚砜与4-取代的1，2，4-三唑啉-3，5-二酮通过[2+ 4]环加成反应合成烷基取代的硫杂环戊二烯亚砜，并进一步证明了这种新型硫杂环戊二烯亚砜的独特结构特征。
1 2 attention has focused on the [2+ 4] cycloaddition of radialenes with dienophiles, no examples are known for [3] radialene2 and its analogue. 3 The addition would be synthetically useful as a means of introducing a double bond into a three-membered ring fused to a six-membered ring, thereby giving a highly strained compound (eq1). Both 1 and 2 can be regarded as potential precursors for the syntheses of six-membered rings fused to thiirene and thiirene sulfoxide units, respectively. We now report the first syntheses of alkyl-substituted thiirene sulfoxides by [2+ 4] cycloaddition of thiiranoradialene sulfoxide with 4-substituted 1, 2, 4-triazoline-3, 5-diones (TAD) and further to demonstrate the uniquestructural features of the novel thiirene sulfoxide so formed.