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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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
Publication:	Tetrahedron
Publisher:	Elsevier Science
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.ac.in/id/eprint/35724

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