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Effects of N-alkyl substitution on the formation and rate-limiting deprotonation of the spiro-meisenheimer intermediate of smiles' rearrangement of 2-(p-nitrophenoxy) ethylamine. by A.C. Knipe; N. Sridhar; J. Lound-Keast is a Chemistry article available to read on EtoBox.

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General base catalysis, and N-alkyl group dependence, of the title rearrangement (which approaches a rate limit at high base concentration) has been interpreted: We recently reported (1) that kinetic studies of intramolecular nucleophilic aromatic displacement of alkoxide ion by the amino group in 2-(p-nitrophenoxy)ethylamine (SH) support a mechanism (SCHEME, R=H) whereby, at low base concentration, the rate of Smiles' rearrangement is dependent upon the rate of general base-catalysed deprotonation of a Spiro-Meisenheimer intermediate (MH);

Who reads Effects of N-alkyl substitution on the formation and rate-limiting deprotonation of the spiro-meisenheimer intermediate of smiles' rearrangement of 2-(p-nitrophenoxy) ethylamine.?

Author

A.C. Knipe; N. Sridhar; J. Lound-Keast

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1979

Language

EN

Field

Chemistry (Physical Sciences)