Dienophilic behavior of the vinylic (C=C) and the carbonyl (C=O) bonds of ketenes in reactions with 1,3-diazabuta-1,3-dienes

被引：25

作者：

Bharatam, PV ^{[1
]}

Kumar, RS

Mahajan, MP

机构：

[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

[2] Guru Nanak Dev Univ, Dept Pharmaceut Sci, Amritsar 143005, Punjab, India

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol000052t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ab initio and density functional studies (DFT) on cycloaddition reactions of 1,3-diazabuta-1,3-dienes with ketenes are reported. The vinylic (C = C) and the carbonyl (C = O) units of the ketenes are found to participate in concerted asynchronous [4 + 2] cycloaddition reactions. The transition states (3t, 4t, and 7t) for these paths have been located on the RE surface at the correlated levels of ab initio calculations. A reasonable mechanism for the formation of [4 + 2] and [2 + 2] adducts is presented.

引用

页码：2725 / 2728

页数：4

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