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The mechanism of the conversion ofo-nitrobenzoyldiazomethane to N-hydroxyisatin

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
20
Issue
9
Identifiers
DOI: 10.1016/s0040-4020(01)98477-7

Abstract

Abstract The acid-catalyzed conversion of o-nitrobenzoyldiazomethane (I) to N-hydroxyisatin (V) has been studied by following the fate of the diazo carbon atom in I which was labelled with C 14. Degradation of V showed that all the C 14 was in the C 2-position, thus establishing that a Wolff-type rearrangement of I (via a ketene intermediate) was not involved in the formation of V. A mechanism for the rearrangement of I to V, differing in important details from the mechanism previously proposed by Moore, 3 has been advanced.

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