Retro Diels–Alder and other electron ionization-induced fragmentation reactions of 1,2,3,4-tetrahydrobenzopyran-2,3-dicarboxylic acid derivatives

Szmigielski, Rafał; Danikiewicz, Witold; Dolatowska, Karolina; Wojciechowski, Krzysztof

doi:10.1016/j.ijms.2005.12.016

Cited by 8 publications

(4 citation statements)

References 11 publications

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“…The criterion of mass spectrometric behavior chosen for rationalization with pseudo‐NMR 13 C‐shifts is γ , the ratio of the sum of cross‐ring cleavage product ion intensities to the sum of ring‐opening product ion signal intensities in the product ion mass spectra observed from flavonoids. Cross‐ring cleavage (CRC) or retro‐Diels‐Alder (RDA)68 reaction competes with ring opening (RO) of the C‐ring in the observed product ion mass spectra from flavonoids.…”

Section: Resultsmentioning

confidence: 99%

A Comparison of the Reactivity of Ni Atoms Toward CH₄, SiH₄, and SnH₄: A Combined Matrix Isolation and Quantum‐Chemical Study

Himmel

2004

Chemistry A European J

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Nickel atoms are shown to react spontaneously with SiH(4) and SnH(4) to give the insertion products HNiSiH(3) and HNiSnH(3). With CH(4), however, no spontaneous reaction occurs, in agreement with earlier reports; HNiCH(3) can be formed only on photolytic activation of the Ni atom. The reaction products were characterized experimentally by IR spectroscopy, including the effect of isotopic substitution (H/D), and by quantum-chemical calculations. They all have C(s) symmetry with a terminal Ni--H bond and three terminal E--H bonds (E=Si, Sn). Strikingly, the H-Ni-E bond angles are less than 90 degrees, and there is a weak interaction between the H atom bound to Ni and the E atom. The structures are compared with those of other molecules of general formula MSiH(4) that have been characterized recently in our group (M=Ti, Ni, Ga). While TiSiH(4) has three Ti-H-Si bridges, both NiSiH(4) and GaSiH(4) exhibit only terminal Ni--H and E--H bonds, but with the difference that there is no interaction between the H atom bound to Ga and the Si atom.

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Section: Resultsmentioning

confidence: 99%

A Comparison of the Reactivity of Ni Atoms Toward CH₄, SiH₄, and SnH₄: A Combined Matrix Isolation and Quantum‐Chemical Study

Himmel

2004

Chemistry A European J

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“…During the course of our investigations on the homo-and heterocyclic fullerene cycloadducts, we have observed that the molecular odd-electron ions generated under ESI conditions and negative mode of detection from substituted isoxazolinofullerenes [25] . On the other hand, the retro-Diels-Alder reaction (RDA) is a wellknown process, which can be generated in a mass spectrometer [26][27][28], and is one of the most investigated spectrometric process in the fullerene chemistry [29][30][31]. A RDA process is observed when substituted tetrahydroquinazolinofullerenes undergo a fragmentation forming as the only product ion the [60]fullerene [32].…”

Section: Introductionmentioning

confidence: 99%

Mass Spectrometry Studies of the Retro-Cycloaddition Reaction of Pyrrolidino and 2-Pyrazolinofullerene Derivatives Under Negative ESI Conditions

Delgado

Filippone

Martín‐Domenech

et al. 2011

J. Am. Soc. Mass Spectrom.

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Substituted pyrrolidino-and 3-alkyl-2-pyrazolinofullerenes ionize under ESI and MALDI mass spectrometry conditions and negative mode of detection undergoing mass spectral fragmentations, which can be easily correlated with the reported results for the thermal and electrochemical retro-cycloaddition reactions of these compounds. 2-Pyrazolinofullerenes lead directly to a [60] fullerene product ion formed through a retro-cycloaddition process regardless of the substituents attached at the carbon and nitrogen atoms of the heterocyclic ring. These results are different from whose reported for the thermal and electrochemical processes. In contrast, pyrrolidinofullerenes undergo different fragmentative reactions depending upon the substituents (hydrogen, alkyl, or acyl) attached at the nitrogen atom of the heterocyclic ring leading eventually to the pristine C 60 in the last step of the fragmentation pathway.

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“…Previously, Szmigielski and Danikiewicz reported the main fragmentation products of 1,2,3,4‐tetrahydroquinoline using an electron ionization (EI) source . Thevis's group analyzed four tricyclic tetrahydroquinoline derivatives using liquid chromatography/electrospray ionization tandem mass spectrometry .…”

Section: The Structures and Main Fragmentation Pathways Of Furo[32‐cmentioning

confidence: 99%

Analysis of furo[3,2‐c]tetrahydroquinoline and pyrano[3,2‐c]tetrahydroquinoline derivatives as antitumor agents and their metabolites by liquid chromatography/electrospray ionization tandem mass spectrometry

Hou

Luo

et al. 2013

Rapid Comm Mass Spectrometry

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Retro Diels–Alder and other electron ionization-induced fragmentation reactions of 1,2,3,4-tetrahydrobenzopyran-2,3-dicarboxylic acid derivatives

Cited by 8 publications

References 11 publications

A Comparison of the Reactivity of Ni Atoms Toward CH₄, SiH₄, and SnH₄: A Combined Matrix Isolation and Quantum‐Chemical Study

A Comparison of the Reactivity of Ni Atoms Toward CH₄, SiH₄, and SnH₄: A Combined Matrix Isolation and Quantum‐Chemical Study

Mass Spectrometry Studies of the Retro-Cycloaddition Reaction of Pyrrolidino and 2-Pyrazolinofullerene Derivatives Under Negative ESI Conditions

Analysis of furo[3,2‐c]tetrahydroquinoline and pyrano[3,2‐c]tetrahydroquinoline derivatives as antitumor agents and their metabolites by liquid chromatography/electrospray ionization tandem mass spectrometry

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Retro Diels–Alder and other electron ionization-induced fragmentation reactions of 1,2,3,4-tetrahydrobenzopyran-2,3-dicarboxylic acid derivatives

Cited by 8 publications

References 11 publications

A Comparison of the Reactivity of Ni Atoms Toward CH4, SiH4, and SnH4: A Combined Matrix Isolation and Quantum‐Chemical Study

A Comparison of the Reactivity of Ni Atoms Toward CH4, SiH4, and SnH4: A Combined Matrix Isolation and Quantum‐Chemical Study

Mass Spectrometry Studies of the Retro-Cycloaddition Reaction of Pyrrolidino and 2-Pyrazolinofullerene Derivatives Under Negative ESI Conditions

Analysis of furo[3,2‐c]tetrahydroquinoline and pyrano[3,2‐c]tetrahydroquinoline derivatives as antitumor agents and their metabolites by liquid chromatography/electrospray ionization tandem mass spectrometry

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A Comparison of the Reactivity of Ni Atoms Toward CH₄, SiH₄, and SnH₄: A Combined Matrix Isolation and Quantum‐Chemical Study

A Comparison of the Reactivity of Ni Atoms Toward CH₄, SiH₄, and SnH₄: A Combined Matrix Isolation and Quantum‐Chemical Study