1, 4‐Diphenyl‐1, 3‐butadiene and 1, 1, 4, 4‐Tetraphenyl‐1, 3‐butadiene in the Reactions of Oxidative Sulfamidation and Trifluoroacetamidation. Issue 17 (13th June 2017)

• Record Type: Journal Article
• Authors: Moskalik, Mikhail Yu.; Astakhova, Vera V.; Sterkhova, Irina V.; Shainyan, Bagrat A.
• Is Part Of: ChemistrySelect. Volume 2:Issue 17(2017)
• Page Start: 4662
• Page End: 4666
• Publication Date: 2017-06-13
• Subjects: 1, 3-butadienes -- oxidative addition/cycloaddition -- rearrangement -- sulfonamides -- trifluoroacetamide; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201701147
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: 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. Abstract : Triflamide, p ‐nitrobenzenesulfonamide and trifluoroacetamide react with 1, 4‐diphenyl‐1, 3‐butadiene and 1, 1, 4, 4‐tetraphenyl‐1, 3‐butadiene under oxidative conditions to give the products of heterocyclization, the triflamide‐induced rearrangement with migration of several phenyl groups, and the C=C bond splitting.