Bulletin of the Korean Chemical Society

  • 제21권6호
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  • Pages.595-603
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  • 2000
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Free Radical-mediated Ring Expansion Reactions:Endocyclic Cleavage of Cyclopropylcarbinyl Radicals

  • 발행 : 20000600
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초록

Ring expansion reactions via endocyclic cleavage of cyclopropylcarbinyl radicals derived from the reaction of [1-benzyloxycarbonylbicyclo[n. 1.O]alk-(n+l)-yl] -1-imidazolethiocarboxylates with tributyltin hydride/AIBN proceeded to produce 3-cycloalkenecarboxylates in good yields. Benzyl (5'-phenoxypentyl) -3-cyclohepten-1 -carboxylate was obtained in 33% yield from the reaction of benzyl 5-methylenebicyclo [4. 1.0]- 1-carboxylates with 4-phenoxybutyl iodide under radical conditions. Selective cleavage of endocyclic bond in cyclopropane to the cyclohexane, results from stabilization of the resultant radical by the carbonyl groups, such as the benzyloxycarbonyl group, which lower the transition state energy for the final cyclopropane cleavage in the ring expansion.

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피인용 문헌

  1. ChemInform Abstract: Free Radical Mediated Ring Expansion Reactions: Endocyclic Cleavage of Cyclopropylcarbinyl Radicals. vol.31, pp.46, 2000, https://doi.org/10.1002/chin.200046055
  2. Fluorine‐Containing Functionalized Cyclopentene Scaffolds Through Ring Contraction and Deoxofluorination of Various Substituted Cyclohexenes vol.2018, pp.27, 2018, https://doi.org/10.1002/ejoc.201800057