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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 2, 1972 - Issue 3
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Original Articles

Synthesis of Adamantane Derivatives. XVIII. On the Bromination of 1- and 3-Homoadamantanecarboxylic Acids. an Improved Synthesis of L-Bromomethyladamantane-3-Carboxylic Acid and Some Derivatives Thereof

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Pages 115-120 | Received 17 Jan 1972, Published online: 26 Jan 2007

References

  • Sasaki , T. , Eguchi , S. and Toru , T. 1971 . J. Org. Chem. , 36 : 3460 Part XVII:
  • Fort , R. C. Jr. and Schleyer , P. v. R. 1964 . Chem. Rev. , 64 : 277 For a review, see
  • Stetter , H. and Wulff , C. 1960 . Chem. Ber. , 93 : 1366 For bromination of adamantane, see
  • Gorrie , T. M. and Schleyer , P. v. R. 1971 . Org. Prep. Proced. Int. , 3 : 159 For dibromination of adamantane, see, and references therein
  • Stetter , H. and Goebel , P. 1963 . Chem. Ber. , 96 : S50 For bridgehead bromination of 3-homoadamantanol with thionyl bromide, see
  • Schleyer , P. v. R. , Lam , L. K. M. , Raber , D. J. , Fry , J. L. , McKervey , M. A. , Alford , J. R. , Cuddy , B. D. , Keizer , V. G. , Gluk , M. W. and Schlatmann , J. L. M. A. 1970 . J. Amer. Chem. Soc. , 92 : S246
  • Stepanov , F. N. and Goots , S. S. 1970 . Izv. Akad. Nauk SSSR, Ser Khim. , 2 : 430 Chem. Abstr., 73, 3S18t (1970); A. G. Yurchenko, F. N. Stepanov and S. S. Isaeva, OTg. Mass Spectrometry, 3, 1401 (1970);
  • Sasaki , T. , Eguchi , S. , Toru , T. and Itoh , K. J. Amer. Chem. Soc. , We have prepared Ila also from 3-homoadamantanol via the corresponding bromide and cyanide, followed by acid hydrolysis:, submitted to Cf. also, F. N. Stepanov and S. S. Isaeva, Zh. Org. Khim., T, 850 (1971), Chem. Abstr., 7S, 48S15x (1971)
  • Stepanov , F. N. , Baklan , V. F. and Isaeva , S. D. 1965 . J. Org. Chem. USSR. , 1 : 270
  • All of the compounds reported had satisfactory analyses except unstable VI and VII; all mps are corrected
  • Stetter , H. , Schwarz , M. and Hirschhorn , A. 1959 . Chem. Ber. , 92 : 1929
  • Fort , R. C. Jr. and Schleyer , P. v. R. 1966 . Advances in Alicyclic Chemistry , Edited by: Hart , H. and Karabatsos , G. J. Vol. 1 , 283 – 370 . New York : Academic Press . For a review on bridgehead reactivity, see
  • Stetter , H. and Mayer , J. 1962 . Chem. Ber. , 9S : 667

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