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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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|
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