Electron Impact Induced Methyl Migration in Dimethylamino Heteroaromatic Systems

Y. Rahamim; M. Sprecher; J. Sharvit; A. Mandelbaum

doi:10.1021/jo01287a030

Electron Impact Induced Methyl Migration in Dimethylamino Heteroaromatic Systems

Y. Rahamim, M. Sprecher, J. Sharvit, A. Mandelbaum

Department of Chemistry

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Abstract

The syntheses of 2-dimethylamino-5-nitropyrimidine (la), 2-di(trideuteriomethyl)amino-5-nitropyrimidine (Ib), and 2-dimethylamino-5-benzenesulfonamidopyrimidine (III) are reported. The mass spectra of la, lb, III, and 6-dimethyIaminopurine (II) are analyzed. Intense peaks M - 29 found in the spectra of la and II are shown to be due to loss of CHgN from the molecular ion. This fragmentation is presumably accompanied by methyl migration from the exo-to the endo-cyclic nitrogen.

Original language	English
Pages (from-to)	3856-3859
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	32
Issue number	12
DOIs	https://doi.org/10.1021/jo01287a030
State	Published - 1967

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title = "Electron Impact Induced Methyl Migration in Dimethylamino Heteroaromatic Systems",

abstract = "The syntheses of 2-dimethylamino-5-nitropyrimidine (la), 2-di(trideuteriomethyl)amino-5-nitropyrimidine (Ib), and 2-dimethylamino-5-benzenesulfonamidopyrimidine (III) are reported. The mass spectra of la, lb, III, and 6-dimethyIaminopurine (II) are analyzed. Intense peaks M - 29 found in the spectra of la and II are shown to be due to loss of CHgN from the molecular ion. This fragmentation is presumably accompanied by methyl migration from the exo-to the endo-cyclic nitrogen.",

author = "Y. Rahamim and M. Sprecher and J. Sharvit and A. Mandelbaum",

year = "1967",

doi = "10.1021/jo01287a030",

language = "אנגלית",

volume = "32",

pages = "3856--3859",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "12",

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T1 - Electron Impact Induced Methyl Migration in Dimethylamino Heteroaromatic Systems

AU - Rahamim, Y.

AU - Sprecher, M.

AU - Sharvit, J.

AU - Mandelbaum, A.

PY - 1967

Y1 - 1967

N2 - The syntheses of 2-dimethylamino-5-nitropyrimidine (la), 2-di(trideuteriomethyl)amino-5-nitropyrimidine (Ib), and 2-dimethylamino-5-benzenesulfonamidopyrimidine (III) are reported. The mass spectra of la, lb, III, and 6-dimethyIaminopurine (II) are analyzed. Intense peaks M - 29 found in the spectra of la and II are shown to be due to loss of CHgN from the molecular ion. This fragmentation is presumably accompanied by methyl migration from the exo-to the endo-cyclic nitrogen.

AB - The syntheses of 2-dimethylamino-5-nitropyrimidine (la), 2-di(trideuteriomethyl)amino-5-nitropyrimidine (Ib), and 2-dimethylamino-5-benzenesulfonamidopyrimidine (III) are reported. The mass spectra of la, lb, III, and 6-dimethyIaminopurine (II) are analyzed. Intense peaks M - 29 found in the spectra of la and II are shown to be due to loss of CHgN from the molecular ion. This fragmentation is presumably accompanied by methyl migration from the exo-to the endo-cyclic nitrogen.

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SN - 0022-3263

VL - 32

SP - 3856

EP - 3859

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

Electron Impact Induced Methyl Migration in Dimethylamino Heteroaromatic Systems

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