Photoinduced electron transfer reactions of α,β-epoxy ketones with 2-phenyl-N,N-dimethylbenzimidazoline (PDMBI): Significant water effect on the reaction pathway

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7079-7082

  Hasegawa, Eietsu ^a   Kato, Teru ^a   Kitazume, Takashi ^a   Yanagi, Kazuhiro ^a   Hasegawa, Kazuya ^a   Horaguchi, Takaaki ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; PHOTOCHEMISTRY;

EID: 0030599278     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01578-X     Document Type: Article

References (29)

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14. 3a
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24. 1H-NMR analysis of the crude reaction mixture. Although isolation and characterization of the oxidized products from PDMBI have not been completed yet, among the compounds detected was N-methyl-N-(2-N'-methylanilino)benzamide, a ring-opened form of 2-hydroxy-PDMBI, that is probably formed through the reaction of imidazolium ion and hydroxy ion (see Scheme 1).
25. 2 and found that neither triethylamine nor tribenzylamine was effective to obtain 2a in high yields.
26. 9. Using dry tetrahydrofuran (distilledfrom Na-benzophenone) for the reactions, we found that the yields of 2a irregularly changed on several entries. Lower yields of 2a appeared to result from the greater formation of 3a. We think that such tricky results indicate that accidental contamination of water (moisture) would influence the product distribution and this could not be easily a voided in the usual preparative experiments.
27. 1H-NMR analysis of the concentrated photolysate. Qualitatively, the amount of acetophenone changed in a similar way to that of 4a upon changing the amount of water added
28. 11b
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