On the Mechanism of the [3+2]-Cycloaddition of Phenylnitroso Oxide to trans-Stilbene

Author(s):

Vitaly S. Khursan, Ekaterina M. Chainikova*, Sergey L. Khursan and Rustam L. Safiullin   Pages 161 - 164 ( 4 )

Abstract:

The non-photolytic method for generation of arylnitroso oxides based on the reduction of nitrosobenzene by triphenylphosphine was used to study the products of the reaction of transphenylnitroso oxide with trans-stilbene. N,α-Diphenylnitrone and benzaldehyde were found to be the main stable products of the reaction, the first stage of which was [3+2]-cycloaddition to form the metastable 1,2,3-dioxazolidine intermediate. The obtained products were in agreement with our previous theoretical predictions.

Keywords:

Phenylnitroso oxide, [3+2]-cycloadditon to stilbene, N, α-Diphenylnitrone formation, photolytic, reduction, styrene.

Affiliation:

Ufa Institute of Chemistry of the Russian Academy of Sciences, Ufa Federal Scientific Center, Ufa, Ufa Institute of Chemistry of the Russian Academy of Sciences, Ufa Federal Scientific Center, Ufa, Ufa Institute of Chemistry of the Russian Academy of Sciences, Ufa Federal Scientific Center, Ufa, Ufa Institute of Chemistry of the Russian Academy of Sciences, Ufa Federal Scientific Center, Ufa

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