Synthesis of Cyclopentane-Fused Oxygen Heterocycles from the Intramolecular Reaction of Alkynes with Cyclopropylcarbene-Chromium Complexes

Journal of Organic Chemistry

Volumn 55, Issue 3, 1990, Pages 786-788

  Herndon, James W ^a   Matasi, Julius J ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN;

EID: 0025342798     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00290a003     Document Type: Article

References (13)

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3. Connor, J. A.; Jones, E. M. J. Chem. Soc., Dalton Trans. 1973, 2119–2124.
4. To a refluxing pot of 1 aqueous dioxane under nitrogen was added via syringe an 0.1 M solution of carbene complex 44 in dioxane. The addition was accomplished via syringe pump over a period of 1 h. The solution was allowed to stir an additional 1 h at 100 C. The green solution was allowed to cool to 25 C and was filtered through silica gel. The solvent was removed from the filtrate on a rotary evaporator. Final purification of the residue after evaporation was achieved by flash chromatography on silica gel.
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7. Acetyl chloride (1.0 equiv) was added via syringe to an 0.1 M solution of chromium acylate complex 73 in dichloromethane at -20 C under nitrogen. The solution was allowed to stir 30 min at -20 C, after which time a solution of the acetylenic alcohol (1.0 equiv) in dichloromethane was added via syringe. The solution was allowed to warm to 0 C and was stirred at this temperature for a period of 1 h. The solvent was removed on a rotary evaporator; final purification of the carbene complex was achieved by flash chromatography on silica gel.
8. Johnson, R. A. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Pike, J. E., Morton, D. R., Eds.; Raven Press: New York, 1985; Vol. 14, pp 131–154.
9. Caton, M. P. L.; Hart, T. W. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Pike, J. E.; Morton, D. R. Eds.; Raven Press: New York, 1985, Vol. 14, 73–129.
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