Bulletin of the Korean Chemical Society

  • 제23권9호
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  • Pages.1218-1242
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  • 2002
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Photoaddition Reactions of Silyl Ketene Acetals with Aromatic Carbonyl Compounds: A New Procedure for β-Hydroxyester Synthesis

  • Yoon, Ung-Chan (Department of Chemistry and Chemistry Institute for Functional Materials,Pusan National University) ;
  • Kim, Moon-Jung (Department of Chemistry and Chemistry Institute for Functional Materials,Pusan National University) ;
  • Moon, Jae-Joon (Department of Chemistry and Chemistry Institute for Functional Materials,Pusan National University) ;
  • Oh, Sun-Wha (Department of Chemistry and Chemistry Institute for Functional Materials,Pusan National University) ;
  • Kim, Hyun-Jin (Department of Chemistry and Chemistry Institute for Functional Materials,Pusan National University) ;
  • Mariano, Patrick S. (Department of Chemistry, University of New Mexico)
  • 발행 : 2002.09.20
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초록

Photochemical reactions of aromatic carbonyl compounds with silyl ketene acetals have been explored. Irradiation of acetonitrile or benzene solutions containing aryl aldehydes or ketones in the presence of silyl ketene acetals is observed to promo te formation of ${\beta}-hydroxyester$, 2,2-dioxyoxetane and 3,3-dioxyoxetane products. The ratios of these photoproducts, which arise by competitive single electron transfer (SET) and classical Paterno-Buchi mechanistic pathways, is found to be dependent on the degree of methyl-substitution on the vinyl moieties of the ketene acetals in a manner which reflects expected alkyl substituent effects on the oxidation potentials of these electron rich donors. An analysis of the product distribution arising by irradiation of a solution containing butyrophenone (6) and the silyl ketene acetal 9, derived from methyl isobutyrate, provides an estimate of the rate constants for the competitive Norrish type Ⅱ, SET and Paterno-Buchi processes occuring. Finally, sequences involving silyl ketene acetal-aryl aldehyde or ketone photoaddition followed by 2,2-dioxyoxetane hydrolysis represent useful procedures for Claisen-condensation type, ${\beta}-hydroxyester$ synthesis.

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참고문헌

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  3. Oxetane Synthesis through the Paternò-Büchi Reaction vol.18, pp.9, 2013, https://doi.org/10.3390/molecules180911384
  4. Photochemical reactions of 1,2-diketones with silyl enol ethers vol.41, pp.1, 2015, https://doi.org/10.1007/s11164-013-1203-3
  5. Photoaddition Reactions of Silyl Ketene Acetals with Aromatic Carbonyl Compounds: A New Procedure for β-Hydroxyester Synthesis. vol.34, pp.9, 2002, https://doi.org/10.1002/chin.200309029
  6. Single Electron Transfer Induced Photoaddition Reactions of Silyl Enol Ether to N-Methylphthalimide vol.28, pp.4, 2002, https://doi.org/10.5012/bkcs.2007.28.4.629
  7. Photoadditions of Silyl Butadienyl Ether to 1,2-Diketones vol.57, pp.1, 2002, https://doi.org/10.5012/jkcs.2013.57.1.9
  8. Comparison of Photoaddition Reactions of Aromatic Carbonyl Compounds with Silyl Thioketene Acetal vs. Silyl Ketene Acetal vol.2, pp.3, 2013, https://doi.org/10.5857/rcp.2013.2.3.76
  9. Comparison of Photochemical Reactions of Aromatic Carbonyl Compounds with a Silyl Ketene Thioacetal and a Silyl Ketene Acetal vol.90, pp.2, 2002, https://doi.org/10.3987/com-14-s(k)69
  10. The Paternò-Büchi reaction - a comprehensive review vol.18, pp.10, 2002, https://doi.org/10.1039/c9pp00148d