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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 1, 1971 - Issue 4
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Original Articles

Synthesis of Adamantane Derivatives. XIX. Aluminum Chloride-Catalyzed Reactions of N-Chloro-1-Adamantylamine Derivatives

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Pages 267-272 | Received 22 Jul 1971, Published online: 06 Feb 2007

References

  • Sasaki , T. , Eguchi , S. and Toru , T. Bull. Chem. Soc. Japan , submitted to Part XVIII
  • Liggero , S. H. , Sustmann , R. and v. Schleyer , P. R. 1969 . J. Amer. Chem. Soc , 91 : 4571 and references therein
  • Kovacic , P. , Liu , J-H. , Roskos , P. D. and Levi , E. M. 1970 . Chem. Commun. , : 1034
  • All new compounds had satisfactory CHN analyses and mps are uncorrected. All chloro compounds had positive Beilstein test
  • Fort , R. C. Jr. and v. Schleyer , P. R. 1965 . J. Org. Chem. , 30 : 739 For nmr study on adamantane series, see
  • No trace amounts of Ia and IIa were detected on TLC.
  • Gassman , P. G. 1970 . Accounts of Chem. Res. , 3 : 26 cf. Although the spin state of 1-adamantylnitrenium ion is not known at present, the reactivity difference between singlet and triplet nitrenium ion is discussed by
  • Krumkalns , E. V. and Pfeifer , W. 1968 . J. Med. Chem. , 11 : 1103
  • Statter , H. , Schwarz , M. and Hirschhorn , A. 1959 . Chem. Ber. , 92 : 1629
  • Stetter , H. , Krause , M. and Last , W.-D. 1968 . Angew. Chem., Internat. Ed. , 7 : 894
  • Ic was prepared from 1-bromoadamantane and aniline, mp 72–74°.
  • Gottwald , E. and Machocsek , H. German Pat., 1,294,371/ . 1969 . Chem. Abstr., 71, 38444b (1969)
  • Kovacic , P. , Lowery , M. K. and Field , K. W. 1970 . Chem. Rev. , 70 : 665
  • Kovacic , P. and Roskos , P. D. 1969 . J. Amer. Chem. Soc. , 91 : 6457

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