BASIC METHANOLYSIS OF BENZOYLMETHYLAMINOPYRIDINES AND THEIR N-OXIDE AND METHYL QUATERNARY DERIVATIVES

被引：2

作者：

BROXTON, TJ ^{[1
]}

DEADY, LW ^{[1
]}

PANG, YT ^{[1
]}

机构：

[1] LA TROBE UNIV,DEPT ORGAN CHEM,BUNDOORA 3083,VICTORIA,AUSTRALIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1978年 / 43卷 / 10期

关键词：

D O I：

10.1021/jo00404a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rate data for the basic methanolysis of PhCON(Me) derivatives of pyridine, pyridine N-oxide, and 1-methylpyridinium iodide are reported. Positional reactivities are 4⨠2>3 (pyridine), 4>3>2 (N-oxide), and 4⨠3 (methylpyridinium). The heterocycles are also considered as substituted N-aryl-N-methylbenzamides; when combined with published data, these results yield a linear Hammett plot (p=3.2). Mechanistic implications of this finding are discussed. © 1978, American Chemical Society. All rights reserved.

引用

页码：2023 / 2026

页数：4

共 16 条

[1] VIBRATION-SPECTRAL AND STRUCTURAL COMPARISON OF 4-AMINOPYRIDINE CATION WITH 4-HYDROXYPYRIDINIUM ION AND 4-PYRIDONE . PROTIO PARENT IONS, N- AND C-DEUTERATED, AND N-METHYLATED IONS . RELEVANT NMR SPECTRAL STUDIES
BATTS, BD
SPINNER, E
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (12) : 2595 - &
[2] STRAIN EFFECTS IN ACYL TRANSFER-REACTIONS .1. KINETICS OF HYDROLYSIS OF SOME N-ARYL-LACTAMS
BLACKBUR.GM
PLACKETT, JD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (10): : 1366 - &
[3] MECHANISM OF BASIC METHANOLYSIS OF BENZANILIDES
BROXTON, TJ
DEADY, LW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (18) : 2767 - 2769
[4] BROXTON TJ, 1975, TETRAHEDRON LETT, P2799
[5] RATES OF BASIC METHANOLYSIS OF SOME N-ALKYL-PARA-NITROACETANILIDES AND 4-(N'-ALKYLACETAMIDO)PYRIDINES
BROXTON, TJ
DEADY, LW
WILLIAMS.PR
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (05) : 1053 - 1057
[6] BASIC METHANOLYSIS OF ANILIDES - EVIDENCE FOR MECHANISM APPLYING TO SPECIAL CASE OF N-METHYL-4'-NITROANILIDES
BROXTON, TJ
DEADY, LW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (20) : 2906 - 2910
[7] DEADY LW, UNPUBLISHED
[8] THE KINETICS OF ALKALINE HYDROLYSIS OF 2-ETHOXYCARBONYLPYRIDINES, 3-ETHOXYCARBONYLPYRIDINES, AND 4-ETHOXYCARBONYLPYRIDINES AND THEIR 1-OXIDES
FALKNER, PR
HARRISON, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR): : 1171 - 1174
[9] N-OXIDES AND RELATED COMPOUNDS .17. THE TAUTOMERISM OF MERCAPTO-PYRIDINE AND ACYLAMINO-PYRIDINE 1-OXIDES
JONES, RA
KATRITZKY, AR
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (JUL): : 2937 - 2942
[10] POTENTIALLY TAUTOMERIC PYRIDINES .2. 2-ACETAMIDO-PYRIDINE,3-ACETAMIDO-PYRIDINE, AND 4-ACETAMIDO-PYRIDINE AND 2-BENZAMIDO-PYRIDINE, 3-BENZAMIDO-PYRADINE, 4-BENZAMIDO-PYRIDINE
JONES, RA
KATRITZKY, AR
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1959, (APR): : 1317 - 1323

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