Mass-spectral rearrangement, photo-isomerization and photo-solvolysis of bis(2-acetylpyrrol-1-yl)methane

Houwen, O.H.; Tavares, Donald F.

doi:10.1016/s0040-4039(01)85791-9

Cited by 8 publications

(2 citation statements)

References 5 publications

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“…The triplet excited state of 25 can bring about an intramolecular hydrogen abstraction to give the biradical intermediate 26 , which can lead to 28 , through other intervening biradical intermediates 29 and 30 . It is interesting to note that none of the N−C bond cleavage product 24 was isolated from this reaction (Scheme ), although N−C cleavage-derived products have been isolated in the phototransformations of N -alkyl-substituted pyrroles …”

Section: Discussionmentioning

confidence: 99%

Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides¹

et al. 1996

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The phototransformations of a few 2,3-diaroylaziridines and 2-aryl-3-aroylaziridines have been studied by steady-state photolysis and product analysis. The formation of various photoproducts could be substantiated by ring opening via C-C bond cleavage (leading to azomethine ylides), intramolecular hydrogen abstraction, and C-N bond cleavage. Isolation of stereospecific 3-pyrroline derivatives from the photoreaction of benzoylaziridines in the presence of DMAD confirms our previous results concerning the azomethine ylides as major transient intermediates, produced under laser pulse photoexcitation. Dimethyl 1-cyclohexyl-2-benzoylpyrrole-3,4-dicarboxylate (25), one of the photoadducts derived from the reaction of 1a and 1b with DMAD undergoes a novel and unusual photorearrangement to give dimethyl 2-(1-benzoylcyclohexyl)pyrrole-3,4-dicarboxylate (27), the structure of which was confirmed through X-ray crystallographic analysis.

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Section: Discussionmentioning

confidence: 99%

Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides¹

et al. 1996

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“…127.4(5 C ( 6 ) -N ( 7 1 ) -C ( 7 2 ) 120.3(5 N ( 7 1 ) -C ( 7 2 ) -C ( 7 3 ) 122.1(5 C ( 7 2 ) -C ( 7 3 ) -C ( 7 4 ) 119.7(5 C ( 7 3 ) -C ( 7 4 ) -N ( 8 ) 121.3(5 C ( 7 3 ) -C ( 7 4 ) -C ( 7 5 ) 115.6(5 C ( 7 4 ) -C ( 7 5 ) -C ( 7 6 ) 121.8(5 C ( 7 5 ) -C ( 7 6 ) -N ( 7 1 ) 120.9(5 C ( 7 5 ) -C ( 7 4 ) -N ( 8 ) 123.1(5 C ( 7 6 ) -N ( 7 1 ) -C ( 7 2 ) 119.7(5 C ( 7 6 ) -N ( 7 1 ) -C ( 6 ) 119.9(5 C ( 7 4 ) -N ( 8 ) -C ( 8 1 ) 121.1(5 C ( 7 4 ) -N ( 8 ) -C ( 8 2 ) 121.6(5 C ( 8 1 ) -N ( 8 ) -C ( 8 2 ) 117.0(5 zu n g e n d ieses Typs sind im S ch em a 7/Tab. V II z u sa m m e n g efaß t.…”

Section: S Elek Tive Substitution Der Triphenylarsoniofunktion Durch mentioning

confidence: 99%

Onio-assistierte S_N2-Reaktionen: Allgemeiner Zugang zu symmetrischen und unsymmetrischen geminal bisoniosubstituierten Methanderivaten / Onio-Assisted S_N2-Reactions: General Access to Symmetrical and Unsymmetrical Geminally Bisonio Substituted Methane Derivatives

Weiß

Handke

Reichel

et al. 1998

Zeitschrift Für Naturforschung B

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O n io -A ssisted SN2 -R ea ctio n s: G e n e ra l A cc ess to S y m m etrical an d U n sy m m e tric a l G e m in a lly B iso n io S u b stitu te d M e th a n e D e riv a tiv e s R o b e rt W eiss*, M a tth ia s H a n d k e , Silvia R e ic h e l, F ra n k H a m p e l S o n d e r d ru c k a n fo rd e ru n g e n an P rof. D r. R. W eiss. T elefax: Int. +9131/859132. E -M a il: rw e iss@ o rg a n ik .u n i-E rla n g e n .d e . Schema 2. a) X = Br, I INu = p-substituierte Pyridine [10] b) X = CI, Br INu = Trialkyl/aryl-phosphane [11] und INu = Trialkyl/aryl-arsane [12]0932-0776/98/0500-0599 $06.00 © 1998 Verlag d e r Z eitschrift für N aturforschung. All rights reserved. Brought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 7/16/15 12:29 PM --

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Physical and Theoretical Aspects, Synthesis, and Chemical Reactivity of 2 H ‐ and 3 H ‐Pyrroles

Sammes¹

1990

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Mass-spectral rearrangement, photo-isomerization and photo-solvolysis of bis(2-acetylpyrrol-1-yl)methane

Cited by 8 publications

References 5 publications

Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides¹

Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides¹

Onio-assistierte S_N2-Reaktionen: Allgemeiner Zugang zu symmetrischen und unsymmetrischen geminal bisoniosubstituierten Methanderivaten / Onio-Assisted S_N2-Reactions: General Access to Symmetrical and Unsymmetrical Geminally Bisonio Substituted Methane Derivatives

Physical and Theoretical Aspects, Synthesis, and Chemical Reactivity of 2 H ‐ and 3 H ‐Pyrroles

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Mass-spectral rearrangement, photo-isomerization and photo-solvolysis of bis(2-acetylpyrrol-1-yl)methane

Cited by 8 publications

References 5 publications

Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides1

Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides1

Onio-assistierte SN2-Reaktionen: Allgemeiner Zugang zu symmetrischen und unsymmetrischen geminal bisoniosubstituierten Methanderivaten / Onio-Assisted SN2-Reactions: General Access to Symmetrical and Unsymmetrical Geminally Bisonio Substituted Methane Derivatives

Physical and Theoretical Aspects, Synthesis, and Chemical Reactivity of 2 H ‐ and 3 H ‐Pyrroles

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Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides¹

Phototransformations of C-Benzoylaziridines. Dipolarophilic Trapping of Photogenerated Azomethine Ylides¹

Onio-assistierte S_N2-Reaktionen: Allgemeiner Zugang zu symmetrischen und unsymmetrischen geminal bisoniosubstituierten Methanderivaten / Onio-Assisted S_N2-Reactions: General Access to Symmetrical and Unsymmetrical Geminally Bisonio Substituted Methane Derivatives