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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 3
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Original Articles

Stereospecific Hydroformylation of endo-Dicyclopentadiene in the Presence of Rhodium Complex Catalysts. A Route to endo-Tricyclo[5.2.1.02,6]Dec-8-exo-Ylcarbinol, Precursor of 4-Homoisotwistane

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Pages 199-207 | Received 11 Dec 1975, Published online: 13 Dec 2006

References

  • Aigami , K. , Inamoto , Y. , Takaishi , N. , Fujikura , Y. , Takatsuki , A. and Tamura , G. J. Med. Chem. , in press
  • Takaishi , N. , Inamoto , Y. , Aigami , K. , Tsuchihashi , K. and Ikeda , H. 1974 . Synth. Commun. , 4 : 225
  • Takaihsi , N. , Inamoto , Y. , Tsuchihashi , K. and Aigami , K. 1975 . Synth. Commun. , 5 : 369
  • Esso Research and Engineering Co. . Brit. Patent 728,913 . 1955 . (Chem. Abstr., 50, 7852e (1956)); K. Büchner and O. Roelen, Ger. Patent, 928, 645 (1955) (Chem. Abstr., 52, 5452c (1958)); Ruhrchemie AG, Brit. Patent, 750,144 (1956)(Chem. Abstr., 51, 9680c (1957)); Brit. Patent, 765,742 (1957) (Chem. Abstr., 51, 12970e (1957)); K. Büchner, O. Roelen, and J. Meis, Ger. Patent, 1,032,241 (1958) (Chem. Abstr., 54, 17294e (1960)).
  • Kaufmann , H. P. and Steffan , G. 1965 . Fette, Seifen, Anstrichm. , 67 : 784
  • Only single example seems to exist of the use of rhodium metal (as oxide) for hydroformylation of endo-dicyclopentadiene: J. Falbe . Ger. Patent, 1,618,384 . 1971 . (Chem. Abstr., 75, 129416t (1971)).
  • Evans , D. , Osborn , J. A. and Wilkinson , G. 1968 . J. Chem. Soc. (A) , : 3113
  • Schleyer , P. v. R. and Donaldson , M. M. 1956 . J. Amer. Chem. Soc. , 78 : 5702
  • Zweifel , G. and Brown , H. C. 1963 . Org. Reactions , 13 : 1 J. A. Marshall and H. Faubl, J. Amer. Chem. Soc., 92, 948 (1970); R. M. Coates and J. P. Chen, Chem. Commun., 1481 (1970); H. C. Brown, I. Rothberg, and D. L. V. Jagt, J. Org. Chem., 37, 4098 (1972); N. Takaishi, Y. Fujikura, and Y. Inamoto, ibid., in press.
  • Wilder, Jr. , P. , Portis , A. R. , Wright , G. W. and Shepherd , J. M. 1974 . J. Org. Chem. , 39 : 1636
  • Structure of the products (II and IIIX) strongly suggests that the coordination of I to rhodium atom occurs at the exo side12of the molecule which functions as a monodentate ligand. This behavior of rhodium is apparently contrasted to those of platinum and palladium on the same ligand.13
  • Fichteman , W. E. and Orohin , M . 1969 . J. Org. Chem. , 34 : 2790 Cf. an exo cis deuteroformylation of 2-norbornene by DCo(CO)4
  • Chatt , J. , Vallarino , L. M. and Venanzi , L. M. 1957 . J. Chem. Soc. , : 2496 ibid., 3413 (1957); J. K. Stille and R. A. Morgan, J. Amer. Chem. Soc., 88, 5135 (1966); also see J. K. Stille and D. E James, ibid., 97, 674 (1975).

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