Stereochemical studies. Part 67. Saturated heterocycles. Part 52. The mass spectra of some condensed skeleton 1,3‐oxazin‐4‐one derivatives

K. Vékey, József Tamás, F. Fülöp, G. Bernáth

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Abstract

The mass spectrometric behaviour of twenty saturated heterocyclic compounds with a 1,3‐oxazin‐4‐one moiety fused with cis or trans anellation to a cycloalkane ring (C5‐C8) was studied. The roles of the C‐2 and N‐3 substituent(s) were found to be characteristic, while the size of the cycloalkane ring seemed to be unimportant. Some fragmentation processes involving breakdown of the oxazinone ring of the cis or trans isomers displayed significant stereoselectivity. A striking new decomposition process involving significant chlorine elimination from the molecular ion of some 2‐p‐chlorophenyl derivatives was observed and was studied in some detail.

Original languageEnglish
Pages (from-to)523-528
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume22
Issue number2
DOIs
Publication statusPublished - 1985

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Cycloparaffins
Derivatives
Heterocyclic Compounds
Stereoselectivity
Chlorine
Isomers
Ions
Decomposition

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Stereochemical studies. Part 67. Saturated heterocycles. Part 52. The mass spectra of some condensed skeleton 1,3‐oxazin‐4‐one derivatives",
abstract = "The mass spectrometric behaviour of twenty saturated heterocyclic compounds with a 1,3‐oxazin‐4‐one moiety fused with cis or trans anellation to a cycloalkane ring (C5‐C8) was studied. The roles of the C‐2 and N‐3 substituent(s) were found to be characteristic, while the size of the cycloalkane ring seemed to be unimportant. Some fragmentation processes involving breakdown of the oxazinone ring of the cis or trans isomers displayed significant stereoselectivity. A striking new decomposition process involving significant chlorine elimination from the molecular ion of some 2‐p‐chlorophenyl derivatives was observed and was studied in some detail.",
author = "K. V{\'e}key and J{\'o}zsef Tam{\'a}s and F. F{\"u}l{\"o}p and G. Bern{\'a}th",
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T1 - Stereochemical studies. Part 67. Saturated heterocycles. Part 52. The mass spectra of some condensed skeleton 1,3‐oxazin‐4‐one derivatives

AU - Vékey, K.

AU - Tamás, József

AU - Fülöp, F.

AU - Bernáth, G.

PY - 1985

Y1 - 1985

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AB - The mass spectrometric behaviour of twenty saturated heterocyclic compounds with a 1,3‐oxazin‐4‐one moiety fused with cis or trans anellation to a cycloalkane ring (C5‐C8) was studied. The roles of the C‐2 and N‐3 substituent(s) were found to be characteristic, while the size of the cycloalkane ring seemed to be unimportant. Some fragmentation processes involving breakdown of the oxazinone ring of the cis or trans isomers displayed significant stereoselectivity. A striking new decomposition process involving significant chlorine elimination from the molecular ion of some 2‐p‐chlorophenyl derivatives was observed and was studied in some detail.

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