1990
DOI: 10.1002/oms.1210251110
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Electron impact and chemical ionization mass spectra of norbornane/ene di‐exo and di‐endo‐fused 1,3‐oxazin‐2(1H)‐ones and 1,3‐oxazine‐2(1H)‐thiones

Abstract: Mass spectral fragmentations of four norbornaneleoe di-em-and di-endo-fused 1,3-oxazin-2( lH)-ones and four 1,3-oxazine-2(1H)-thiones were examined by means of metastable ion analysis, the collision-induced dissociation technique and exact mass measurement. Under electron impact (EI) conditions all the saturated compounds gave rise to complicated fragmentations, including several rearrangements. For the unsaturated compounds, a retro-Diels-Alder (RDA) process was the most favoured fragmentation pathway, which … Show more

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Cited by 16 publications
(3 citation statements)
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“…Surprisingly, the corresponding heterocyclic fragment ions were almost totally absent from the spectra of norbornene-fused 1,3-oxazine-2(1H)-ones and showed only a moderate abundance in the spectra of the thione analogs. 2 The same type of RDA fragmentation was operational in norbornene-fused 1,3-oxazines 2 and 6 ( Fig. 1(b) and Fig.…”
Section: Resultsmentioning
confidence: 78%
See 1 more Smart Citation
“…Surprisingly, the corresponding heterocyclic fragment ions were almost totally absent from the spectra of norbornene-fused 1,3-oxazine-2(1H)-ones and showed only a moderate abundance in the spectra of the thione analogs. 2 The same type of RDA fragmentation was operational in norbornene-fused 1,3-oxazines 2 and 6 ( Fig. 1(b) and Fig.…”
Section: Resultsmentioning
confidence: 78%
“…2 This process occurred with hydrogen transfer from the dienophilic (heterocyclic) part of the molecule to yield abundant cyclopentadiene cation radicals C 5 H 6 + .…”
Section: Resultsmentioning
confidence: 99%
“…The electron ionisation (EI) induced fragmentation of polycyclic rings fused together, and/or to aromatic or heterocyclic rings, is often accompanied by complex fission processes, which are in most cases the result of retro‐Diels‐Alder (RDA) reactions 1–3. An interesting case is provided by the mass spectrum of 1 which showed formation of an ion of m/z 222 4.…”
Section: Methodsmentioning
confidence: 99%