Issue 0, 1986
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Radical-nucleophilic (SRN1) reactions. Part 4. Preparation, reactions, and electron spin resonance studies of α-nitro azides

Suleiman I. Al-Khalil,   W. Russell Bowman  and  Martyn C. R. Symons  

Abstract

2-Azido-2-nitropropane and 1-azido-1-nitrocyclohexane have been prepared by syntheses involving intermediate radicai-anions (SRN1 and oxidative addition). SRN1 Reactions between α-nitroazides and azide, benzenesulphinate, and p-chlorobenzenethiolate proceed with loss of nitrite. The SRN1 reaction between 1-azido-1-nitrocyclohexane and the anion of 2-nitropropane proceeds with loss of azide. Reactions between 2-azido-2-nitropropane and the anions of 2-nitropropane and diethyl ethylmalonate yield oxidative dimerisation. E.s.r. spectroscopy has been used to observe electron-capture by 2-azido-2-nitropropane and its dissociation to nitrite and an ill-defined radical which may be (Me2CN3)·. The addition of benzenesulphinate and the anion of 2-nitropropane to Me2ĊNO2, formed by a minor dissociation route from [Me2C(N3)NO2]–˙, has been observed by e.s.r. spectroscopy.

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Article information

DOI
https://doi.org/10.1039/P19860000555
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 555-565

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Radical-nucleophilic (SRN1) reactions. Part 4. Preparation, reactions, and electron spin resonance studies of α-nitro azides

S. I. Al-Khalil, W. R. Bowman and M. C. R. Symons, J. Chem. Soc., Perkin Trans. 1, 1986, 555 DOI: 10.1039/P19860000555

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