Studies in organic mass spectrometry II. Oxygen rearrangement in the enol ethers of acyclic 1, 3‐diketones

Vandewalle, M.; Schamp, N.; Francque, M.

doi:10.1002/bscb.19660751117

Bulletin des Soc Chimique

1966

DOI: 10.1002/bscb.19660751117

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Studies in organic mass spectrometry II. Oxygen rearrangement in the enol ethers of acyclic 1, 3‐diketones

M. Vandewalle¹,

N. Schamp²,

M. Francque³

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1968

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Cited by 4 publications

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Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen.—I Methoxygruppenwanderungen in den Massenspektren der Methyläther von linearen und verzweigten aliphatischen Polyalkoholen

Grützmacher¹,

Winkler²

1968

Org. Mass Spectrom.

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Abstract-The formation of 1 ,l-dimethoxy-alkyl rearrangement ions in the mass spectra of methyl ethers of linear diols, 1,2,3-trioIs and of derivatives of pentaglycerol and pentaerythritol has been investigated by deuterium labelling and mass measurements. Methoxy group migrations do not occur, or at least only to a small amount, in the mass spectra of the diol-dimethyl ethers. The mass spectra of methyl ethers of 1,2,3-triols exhibit characteristic peaks of the rearrangement ions +CH(OCH,)B and +CR(OCH3)z. These ions arise by a 1,3-migration of a methoxy group, probably during a one step degradation of the molecular ion to give a molecule methyl alkenyl ether and a H-atom or alkyl radical as neutral fragments. Large peaks of the rearrangement ion +CH(OCH& are observed in the mass spectra of compounds of the following type:

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Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen.—I Methoxygruppenwanderungen in den Massenspektren der Methyläther von linearen und verzweigten aliphatischen Polyalkoholen

Grützmacher¹,

Winkler²

1968

Org. Mass Spectrom.

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Bond formation upon electron—impact

Cooks

1969

Org. Mass Spectrom.

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Studies in organic mass spectrometry—VI. The fragmentation of enol derivatives of acyclic β‐diketones

Vandewalle

Schamp

Francque

1969

Org. Mass Spectrom.

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Abstract-The mass spectra of enol derivatives of B-diketones, such as enol ethers and enamines are discussed. Their behaviour under electron-impact is in accordance with the fragmentation we suggested for an acyclic /3-diketone in the enol form.Rearrangement of the enol functional group is observed in the spectra. This process is a general one, as it shows not only migration of oxygen and nitrogen in the enol ethers and enamines, but also migration of sulphur and chlorine in the thio-ether and in 4-chloro-3-pentene-2-one.Enol derivatives are suitable compounds for determining the branching of alkyl chains in Bdiketones.THE DEGRADATION under electron-impact of @-diketones depends largely on the tautomeric e q~i l i b r i u m .~*~*~ In previous papers an attempt was made to differentiate typical fragmentations of both enol-and diketo-molecular ions.lS2 In this context the fragmentation of enol derivatives like enol ethers and enamines of several 1,3-diketones was investigated. En01 ethersStructure A.The mass spectrum OR, 0of 4-methoxy-3-pentene-2-one (I: R, = R, = R, = Me;. .

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Studies in organic mass spectrometry II. Oxygen rearrangement in the enol ethers of acyclic 1, 3‐diketones

Cited by 4 publications

References 1 publication

Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen.—I Methoxygruppenwanderungen in den Massenspektren der Methyläther von linearen und verzweigten aliphatischen Polyalkoholen

Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen.—I Methoxygruppenwanderungen in den Massenspektren der Methyläther von linearen und verzweigten aliphatischen Polyalkoholen

Bond formation upon electron—impact

Studies in organic mass spectrometry—VI. The fragmentation of enol derivatives of acyclic β‐diketones

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