Premium
1,4‐Diphenyl‐1,3‐butadiene and 1,1,4,4‐Tetraphenyl‐1,3‐butadiene in the Reactions of Oxidative Sulfamidation and Trifluoroacetamidation
Author(s) -
Moskalik Mikhail Yu.,
Astakhova Vera V.,
Sterkhova Irina V.,
Shainyan Bagrat A.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701147
Subject(s) - 1,3 butadiene , chemistry , yield (engineering) , oxidative phosphorylation , medicinal chemistry , organic chemistry , catalysis , materials science , biochemistry , metallurgy
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(3 H )‐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.