Synthesis of 8-membered carbocyclic compound having...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C549S383000, C549S386000

Reexamination Certificate

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06872840

ABSTRACT:
The present invention relates to a synthesis of an 8-membered carbocyclic compound having diexomethylene groups, more particularly to a synthesis of an 8-membered carbocyclic compound having diexomethylene groups, a novel compound having the structure represented by the following Chemical Formula 1, from trimethylsilanylmethyl-allenol derivative by the intramolecular Prins cyclization using Lewis acid. The 8-membered carbocyclic compound is a useful intermediate for synthesis of other multicarbocyclic compounds.In Chemical Formula 1, R1is a phenyl group, and R2and R3is a hydrogen atom, or R1, R2and R3may be connected with neighboring substituents to form a 5 to 10-membered aliphatic or aromatic ring.

REFERENCES:
Article “The 91stNational Meeting of the Korean Chemical Society”, ISSN 1229-6708, Apr. 18-19, 2003, p. 363.
Paul A. Wender, et al., “Transition Metal-Catalyzed [6+2] Cycloadditions of 2-Vinylcyclobutanones and Alkenes: A New Reaction for the Synthesis of Eight-Membered Rings”, J. Am. Chem. Soc., vol. 122, No. 32, 2000 American Chemical Society, pp. 7815-7816.
Scott R. Gilbertson, et al., “Rhodium Catalyzed [4+2+2] Cycloaddition and Alkyne Insertion: A New Route to Eight-Membered Rings”, J. Am. Chem. Soc., vol. 124, No. 30, 2002, American Chemical Society, pp. 8784-8785.

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