Kinetics of the Reaction of 2-Nitropropane with Methylenebisamines. A Study of the Mannich Reaction

J. E. Fernandez, Joanna S. Fowler

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The Mannich reactions of 2-nitropropane with methylenebispiperidine and with methylenebismorpholine exhibit second-order kinetics, first order in each component. The 2-nitropropane reacts through the aci form. The rate increases with increasing dielectric constant, and decreases in basic media. Methylenebispiperidine exhibits a faster rate than methylenebismorpholine. The greater reactivity of the piperidine derivative is attributed to its greater base strength. Mechanisms are presented for media of low and high dielectric constant.

Original languageEnglish
Pages (from-to)402-407
Number of pages6
JournalJournal of Organic Chemistry
Volume29
Issue number2
DOIs
StatePublished - 1 Feb 1964
Externally publishedYes

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