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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

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

Volume 16, Issue 3, 2019

Page: [161 - 164] Pages: 4

DOI: 10.2174/1570178615666180830111726

Price: $65

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.

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