Evidence for an aryl migration during the electron impact induced fragmentation of substituted aryloxymethylquinoxalines

Starke, Ines; Sarodnick, Gerhard; Ovcharenko, Vladimir V.; Pihlaja, Kalevi; Kleinpeter, Erich

doi:10.1002/rcm.558

Cited by 6 publications

(1 citation statement)

References 24 publications

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“…The structure of 13a , b is further characterized by the presence of the ion at m/z 281 (cf. Scheme ); this ion has the elemental composition C 18 H 19 NO

_{2}^{+}

and results from rearrangement reactions involving aryl migration 58–60…”

Section: Resultsmentioning

confidence: 99%

Molecular Evolution Using Intramolecular Acyl Migration on myo‐Inositol Benzoates with Thermodynamic and Kinetic Selectors

Ahn

Chang

2004

Chemistry A European J

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A molecular evolution model was successfully demonstrated by combining the intramolecular acyl migration on inositol tribenzoates and boron selectors. The addition of boric acid to 12 members of DCL (dynamic combinatorial library) induced the dramatic amplification of myo-I(2,4,6)Bz(3) (1) with up to 94 % under thermodynamic (see Figure 1 c) control while a portion of phenyl boronic acid caused two significant different distributions: under kinetic control, the pre-equilibrium of DCL shifted to induce the exclusive amplification of 1,4,6-tribenzoyl myo-inositol (7) with decrease of other members up to 82 % from the mixture (see Figure 2 b), and changed gradually to form 2,4,6-tribenzoyl myo-inositol (1) with up to 96 % under thermodynamic control (Figure 2 c).

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“…The structure of 13a , b is further characterized by the presence of the ion at m/z 281 (cf. Scheme ); this ion has the elemental composition C 18 H 19 NO

_{2}^{+}

and results from rearrangement reactions involving aryl migration 58–60…”

Section: Resultsmentioning

confidence: 99%

Molecular Evolution Using Intramolecular Acyl Migration on myo‐Inositol Benzoates with Thermodynamic and Kinetic Selectors

Ahn

Chang

2004

Chemistry A European J

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Current literature in mass spectrometry

2002

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (4 Weeks journals ‐ Search completed at 20th. Feb. 2002)

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Mass spectra of tetrahydroisoquinoline‐fused 1,3,2‐O,N,P‐ and 1,2,3‐O,S,N‐heterocycles: influence of ring size and fusion, of present heteroatoms, substituent effects and of the stereochemistry on fragmentation

Starke

Schuster

Fülöp

et al. 2008

Rapid Comm Mass Spectrometry

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The electron ionization (EI) mass spectra of a variety of stereoisomeric tricyclic 1,3,2-oxazaphosphino[4,3-a]isoquinolines (1-4), 1,2,3-oxathiazino[4,3-a]isoquinoline-4-oxides (5-7) and the -4,4-dioxides (8-10) of oxazaphospholo- and oxathiazolo[4,3-a]- (11, 12, 15 and 16) and -[3,4-b]isoquinolines (13, 14 and 17) were recorded. Ring size and fusion, the different heteroatoms (P and S) and substituents on the ring systems strongly influence the mass spectra. In addition, mass spectra of the stereoisomers of compounds 1, 2 and 13, 14 revealed stereochemically relevant differences which are not observed for the other pairs of isomers.

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Evidence for an aryl migration during the electron impact induced fragmentation of substituted aryloxymethylquinoxalines

Cited by 6 publications

References 24 publications

Molecular Evolution Using Intramolecular Acyl Migration on myo‐Inositol Benzoates with Thermodynamic and Kinetic Selectors

Molecular Evolution Using Intramolecular Acyl Migration on myo‐Inositol Benzoates with Thermodynamic and Kinetic Selectors

Current literature in mass spectrometry

Mass spectra of tetrahydroisoquinoline‐fused 1,3,2‐O,N,P‐ and 1,2,3‐O,S,N‐heterocycles: influence of ring size and fusion, of present heteroatoms, substituent effects and of the stereochemistry on fragmentation

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