1,4-Diphenyl-1,3-butadiene and 1,1,4,4-Tetraphenyl-1,3-butadiene in the Reactions of Oxidative Sulfamidation and Trifluoroacetamidation

被引：11
|
作者：
Moskalik, Mikhail Yu. [1 ]
Astakhova, Vera V. [1 ]
Sterkhova, Irina V. [1 ]
Shainyan, Bagrat A. [1 ]
机构：
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk, Russia
来源：
CHEMISTRYSELECT | 2017年 / 2卷 / 17期
基金：
俄罗斯基础研究基金会;
关键词：
1,3-butadienes; oxidative addition/cycloaddition; rearrangement; sulfonamides; trifluoroacetamide; PINACOL REARRANGEMENT; TRIFLUOROMETHANESULFONAMIDE; AZIRIDINES; FRAMEWORK; ALDEHYDES; ALKENES;
D O I：
10.1002/slct.201701147
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Sulfonamides react with 1,4-diphenyl-1,3-butadiene in oxidative conditions to give the products of heterocyclization, substituted N-sulfonylpyrrolidines. In contrast, 1,1,4,4-tetraphenyl-1,3-butadiene with triflamide in the same conditions unexpectedly gives only 3,4,5,5-tetraphenyldihydrofuran-2(3H)-one as a result of oxidation/heterocyclization with migration of several phenyl groups. Oxidative trifluoroacetamidation of 1,4-diphenyl-1,3-butadiene leads to a similar product of heterocyclization, N-(trifluoroacetyl)pyrrolidine, but also to the product of oxyamidation at only one double bond and, unexpectedly, the product of splitting of the C=C bond, N,N'-(phenylmethanediyl) bis(trifluoroacetamide), in a high total yield. Tentative mechanisms of the reactions are proposed.
引用
收藏
页码：4662 / 4666
页数：5
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