On the Mechanism of the [3+2]-Cycloaddition of Phenylnitroso Oxide to trans-Stilbene
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Published:2019-02-11
Issue:3
Volume:16
Page:161-164
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ISSN:1570-1786
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Container-title:Letters in Organic Chemistry
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language:en
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Short-container-title:LOC
Author:
Khursan Vitaly S.1, Chainikova Ekaterina M.1, Khursan Sergey L.1, Safiullin Rustam L.1
Affiliation:
1. Ufa Institute of Chemistry of the Russian Academy of Sciences, Ufa Federal Scientific Center, Ufa, Russian Federation
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.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry
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