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

J. E. Fernandez; Joanna S. Fowler

doi:10.1021/jo01025a037

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 journal › Article › peer-review

7 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 language	English
Pages (from-to)	402-407
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	29
Issue number	2
DOIs	https://doi.org/10.1021/jo01025a037
State	Published - 1 Feb 1964
Externally published	Yes

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title = "Kinetics of the Reaction of 2-Nitropropane with Methylenebisamines. A Study of the Mannich Reaction",

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.",

author = "Fernandez, \{J. E.\} and Fowler, \{Joanna S.\}",

year = "1964",

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pages = "402--407",

journal = "Journal of Organic Chemistry",

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T1 - Kinetics of the Reaction of 2-Nitropropane with Methylenebisamines. A Study of the Mannich Reaction

AU - Fernandez, J. E.

AU - Fowler, Joanna S.

PY - 1964/2/1

Y1 - 1964/2/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0040603592

U2 - 10.1021/jo01025a037

DO - 10.1021/jo01025a037

M3 - Article

AN - SCOPUS:0040603592

SN - 0022-3263

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SP - 402

EP - 407

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

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

Abstract

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