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Reaction of spironaphthalenones with hydroxylamine: Part III. A novel mechanism for the formation of products and trapping of an intermediate.

Kasturi, Tirumalai R and Kumar, Kaipenchery A and Pragnacharyulu , Palle VP (1993) Reaction of spironaphthalenones with hydroxylamine: Part III. A novel mechanism for the formation of products and trapping of an intermediate. In: Tetrahedron, 49 (1). pp. 135-140.

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)80513-5

Abstract

A mechanism involving the intermediacy of nitrene 5, formed from the oxime of spironaphthalenone 1 by acid catalysed dehydration, has been proposed to explain the formation of pyrrolotropones/pyrrolo esters from spironaphthalenones. The initially formed nitrene rearranges to the isopyrrole 6, which either undergoes sigmatropic migration to the pyrrolotropone 2 or adds alcohol to form the pyrrolo ester depending on substitution at 1′ position. The isopyrrole intermediate 6 has been trapped as a Diels-Alder adduct 8.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 24 Feb 2011 05:00
Last Modified: 24 Feb 2011 05:00
URI: http://eprints.iisc.ernet.in/id/eprint/35724

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