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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 16
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Original Articles

ABOUT THE REACTION OF 2,3-DIBROMO-2-METHYL-N-(1-ADAMANTYL)-PROPANAMIDE WITH SODIUM TERT-BUTOXIDE. A COMPETITION EXPERIMENT

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Pages 2499-2506 | Received 10 Nov 2000, Published online: 09 Nov 2006

REFERENCES

  • Sheehan , J. C. and Lengyel , I. 1964 . The Synthesis and Reactions of an α-Lactam, 1-t-Butyl-3,3-dimethylaziridinone . J. Amer. Chem. Soc. , 86 : 1356 – 1359 .
  • Lengyel , I. , Cesare , V. and Karram , H . 2000 . For a recent report of the synthesis of 1-triphenylmethyl-3-tert-butylaziridinone from the corresponding α-bromoamide with NaOtBu in ether at 0°C in 93% yield see: Synthesis and Some Reactions of an α-Lactam, 1-Triphenylmethyl-3-tert-butyl-aziridinone . 220th National Meeting of the American Chemical Society . August 20–24 2000 , Washington, D.C.. Abstract of Papers, Paper 403553
  • Scrimin , P. , D'Angeli , F. and Veronese , A. C. 1982 . The other one is the phase-transfer catalysis method introduced by Phase-Transfer-Catalyzed Reactions of α-Haloamides: Synthesis of α-Lactams . Synthesis , : 586 – 587 .
  • Backes , J. 1991 . 2-Oxoazetidine (β-Lactame), in Houben-Weyl, Methoden der Organischen Chemie,Vierte Auflage, Band E16b 31 – 867 . Stuttgart, New York : Georg Thieme Verlag .
  • Okawara , T. , Noguchi , Y. , Matsuda , T. and Furukawa , M. 1981 . Convenient Syntheses of Piperazine-2,5-diones and Lactams from Halocarboxamides Using Phase Transfer Catalysts . Chem. Lett. , : 185 – 188 .
  • Lengyel , I. and Sheehan , J. C. 1968 . α-Lactame, Angew. Chem. , 80 : 27 – 38 .
  • Backes , J. 1991 . 2-Oxo-aziridine (α-Lactame) und deren Derivate, in Houben- Weyl, Methoden der Organischen Chemie Vierte Auflage, Band E16b 1 – 19 . Stuttgart, New York : Georg Thieme Verlag .
  • Lengyel , I. and Aaronson , M. J. 1974 . Substituent Interaction and Stereochemical Effects in the Electron-Impact Induced Fragmentation of N-Adamantyl Bromoamides . Can. J. Spectroscopy , 19 : 95 – 99 .
  • Kevill , D. N. and Weitl , F. L. 1970 . Synthesis of 5-Substituted 1-(1-Adamantyltetrazoles and Related Compounds . J. Org. Chem. , 35 : 2526 – 2529 .
  • Stetter , H. , Mayska , P. and Wieβner , U. 1982 . Neue Synthesen und Reaktionen in der Adamantan-Reihe Westdeutscher Verlag, Opladen : Forschungsbericht des Landes Nordrhein- Westfalen Nr. 3095 .

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