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Issue 7, 1976
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Reaction of dinitrogen trioxide with 2-methylpropene and other alkenes. Evidence for electrophilic nitrosation

Abstract

The solid dimer product from the reaction of dinitrogen trioxide and 2-methylpropene was converted to the corresponding oxime by heating with or without a solvent for ca. 2 days. This establishes the orientation of the dinitrogen trioxide addition product as the 1-nitroso- rather than the 2-nitroso-compound as previously thought. A number of other alkene–dinitrogen trioxide adducts have been prepared; most were shown by i.r. spectroscopy to exist partially in the oxime form, the fraction of oxime increasing on warming or on standing for a long time. Hydrolysis of two of the adducts gave products which were in accord with the suggested orientation. There was a striking analogy between these results and those obtained by other workers who examined the products of addition of dinitrogen tetraoxide (acting as nitrosonium nitrate) with alkenes, and their hydrolysis products.

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Article type: Paper
DOI: 10.1039/P29760000828
J. Chem. Soc., Perkin Trans. 2, 1976, 828-832

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    Reaction of dinitrogen trioxide with 2-methylpropene and other alkenes. Evidence for electrophilic nitrosation

    J. R. Park and D. L. H. Williams, J. Chem. Soc., Perkin Trans. 2, 1976, 828
    DOI: 10.1039/P29760000828

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