New insights into the bifunctionality of vanadium phosphorous oxides: A chemical switch between oxidative scission and pinacol rearrangement of vicinal diols

Upadhyaya, Dharita J.; Samant, Shriniwas D.

doi:10.1016/j.cattod.2012.10.021

Cited by 6 publications

(1 citation statement)

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“…Differently substituted epoxides suffer InCl 3 ‐induced ring opening followed by rearrangement resulting in the formation of ketones or aldehydes in quantitative yield . Similarly, vicinal diols undergo the iron‐ or vanadium‐catalyzed rearrangement to the corresponding ketones (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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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-1,3butadiene 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-1,3butadiene 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.

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Section: Introductionmentioning

confidence: 99%