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Racemization in the Camphene Hydrochloride—Isobornyl Chloride Rearrangement1,2

Cite this: J. Am. Chem. Soc. 1953, 75, 13, 3168–3172
Publication Date (Print):July 1, 1953
https://doi.org/10.1021/ja01109a038
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This article is cited by 15 publications.

  1. Jing Kong, Paul v. R. Schleyer and Henry S. Rzepa . Successful Computational Modeling of Isobornyl Chloride Ion-Pair Mechanisms. The Journal of Organic Chemistry 2010, 75 (15) , 5164-5169. https://doi.org/10.1021/jo100920e
  2. Henry S. Rzepa and Charlotte S. M. Allan. Racemization of Isobornyl Chloride via Carbocations: A Nonclassical Look at a Classic Mechanism. Journal of Chemical Education 2010, 87 (2) , 221-228. https://doi.org/10.1021/ed800058c
  3. Ted S. Sorensen. Terpene rearrangements from a superacid perspective. Accounts of Chemical Research 1976, 9 (7) , 257-265. https://doi.org/10.1021/ar50103a003
  4. Clement A. Stone, Mary L. Torchiana, Katherine L. Meckelnberg, John. Stavorski, Meyer. Sletzinger, Gustav A. Stein, William V. Ruyle, Donald F. Reinhold, Walter A. Gaines, Heinz. Arnold, and Karl. Pfister. Chemistry and Structure-Activity Relationships of Mecamylamine and Derivatives. Journal of Medicinal and Pharmaceutical Chemistry 1962, 5 (4) , 665-690. https://doi.org/10.1021/jm01239a001
  5. A. F. Thomas. The Synthesis of Monoterpenes. 2007,,, 1-195. https://doi.org/10.1002/9780470129654.ch1
  6. Weiguo Liu. Terpenes. 2005,,, 59-74. https://doi.org/10.1201/9781420027303.ch5
  7. I. V. Shchirina-�ingorn, L. G. Kuz'mina, A. G. Makarovskaya, Yu. T. Struchkov, I. I. Kritskaya. Rearrangement of 1-chlorocamphene in the presence of boron fluoride and the molecular structure of camphene-4-mercuric chloride. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 1983, 32 (2) , 337-341. https://doi.org/10.1007/BF00957945
  8. Wolfgang Kreiser, Lothar Janitschke. Erste Totalsynthese von (−)-„Alben”. Chemische Berichte 1979, 112 (2) , 408-422. https://doi.org/10.1002/cber.19791120203
  9. Günther W. Hana, Heinrich Koch. Synthesen in der Isocamphanreihe, 10. Synthese von (±)- und erstmals reinem (−)-Camphen. Chemische Berichte 1978, 111 (7) , 2527-2532. https://doi.org/10.1002/cber.19781110707
  10. G. Buchbauer. Die totalsynthese von isosantalol. Tetrahedron Letters 1977, 18 (1) , 7-8. https://doi.org/10.1016/S0040-4039(01)92535-3
  11. Marc Julia, Daniel Mansuy, Patrick Detraz. Oxydation du camphene par le perbenzoate de t-butyle, catalysee par des sels de cuivre. Synthese de l'alcool nojigiku.. Tetrahedron Letters 1976, 17 (25) , 2141-2144. https://doi.org/10.1016/S0040-4039(00)93141-1
  12. S. Rengaraju, K.Darrell Berlin. Mechanism of decomposition of a phosphorylated triazoline. Tetrahedron 1971, 27 (12) , 2399-2407. https://doi.org/10.1016/S0040-4020(01)90743-4
  13. Friedrich Weygand, Hans Grisebach. Die Anwendung von Isotopen in der organischen Chemie. ,,, 108-186. https://doi.org/10.1007/BFb0051895
  14. Walter Hückel, Carl-Martin Jennewein, Hans-Joachim Kern, Otto Vogt. Änderungen des Molekülbaus bei chemischen Reaktionen, XX1) Solvolyse von Toluolsulfonsäureestern, XXVIII1) Konkurrenz- und Folgereaktionen bei der Wagner-Meerwein-Umlagerung Solvolyse von Bornyl- undendo-Fenchyltosylat. Justus Liebigs Annalen der Chemie 1968, 719 (1) , 157-168. https://doi.org/10.1002/jlac.19687190118
  15. G.E. Gream, D. Wege. The structures of the lactones from the action of lead tetra-acetate on camphene, and from acid on tricycloekasantalic acid. Tetrahedron 1966, 22 (8) , 2583-2597. https://doi.org/10.1016/S0040-4020(01)99051-9

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