Bulletin of the Korean Chemical Society

  • 제13권2호
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  • Pages.176-179
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  • 1992
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Transformation of Bicyclic Ketal Compound to 1,2-Cyclopentanediol via 1,5-Diketone

  • 발행 : 1992.04.20
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초록

New method for preparing cyclopentanediol from bicyclic ketal is described. Bicyclic ketal is cleaved to give 1,5-diketone, which is then reductively coupled intramolecularly to yield 1,2-cyclopentanediol. A solution of bicyclic ketal (1a) in methylene chloride was treated with aluminum chloride(2 eq.)-sodium iodide(l.5 eq.) at ambient temperature for 3 h to give the 1,5-diketone (2a) in 71% yield after basic work-up followed by short path column chromatography. A solution of the 1,5-diketone (2a) in THF was reacted with titanium tetrachloride(6 eq.)-Mg(Hg)(0.3 eq.) at $0^{\circ}C$ for 4 h to give the 1,2-cyclopentanediol (3a) in 75% yield after basic work-up followed by short path column chromatography.

키워드

참고문헌

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피인용 문헌

  1. Superbase‐Promoted Selective Cascade Cyclization Reaction of 1,5‐Diketones with Acetylenes to Methylene‐6,8‐dioxabicyclo[3.2.1]octanes vol.2013, pp.12, 1992, https://doi.org/10.1002/ejoc.201201700
  2. New reactions of alkynes with ketones in superbasic media vol.62, pp.11, 1992, https://doi.org/10.1007/s11172-013-0332-6
  3. Reactions of acetylenes in superbasic media. Recent advances vol.83, pp.7, 2014, https://doi.org/10.1070/rc2014v083n07abeh004425
  4. 1,5-Hydrogen Atom Transfer/Surzur-Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems vol.86, pp.21, 1992, https://doi.org/10.1021/acs.joc.1c01376