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Chemistry of the phenoxathiins and isosterically related heterocycles. XXXIII . The influence of intramolecular sulfur-nitro group interactions on the reactivity at sulfur

Mehta, M. U., Martin, G. E. and Smith, Keith 1987. Chemistry of the phenoxathiins and isosterically related heterocycles. XXXIII . The influence of intramolecular sulfur-nitro group interactions on the reactivity at sulfur. Journal of Heterocyclic Chemistry 24 (1) , pp. 235-237. 10.1002/jhet.5570240144

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Abstract

Nitro-groups positioned ortho to thio-esters have been shown to engage in strong, non-bonded intramolecular interactions between the sulfur atom and one of the nitro-group oxygens. The effect of the sulfur-nitro group oxygen interaction on the chemical reactivity at the sulfur atom of 9-nitro-1-azaphenoxathiin is reported. Conditions which normally produce the sulfone exclusively have been shown to yield the sulfoxide with only a minimal quantity of the sulfone produced. Protracted periods of reflux are required to produce the sulfone from the sulfoxide.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: This paper also represents Part 29 in the series Novel Heterocyclic Compounds.
Publisher: Wiley
ISSN: 1943-5193
Last Modified: 04 Jun 2017 03:36
URI: http://orca.cf.ac.uk/id/eprint/23505

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