Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 22
64
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

A Convenient Method for the Preparation of 4(e)-Hydroxy-and 4(e)-Methoxyadamantan-2-ones

, &
Pages 3529-3536 | Received 15 Oct 1990, Published online: 24 Oct 2006

References

  • Faulkner , D. and McKervey , M. A. 1971 . J. Chem. Soc. (C) , : 3906
  • Grob , C. A. , Wittwer , G. and Rao , K. R. 1985 . Helv. Chim. Acta , 68 : 760
  • Henkel , J. G. and Spector , J. H. 1983 . J. Org. Chem. , 48 : 3657
  • Snatzke , G. and Eckhardt , G. 1970 . Tetrahedron , 26 : 1143
  • Duddeck , H. , Feuerhelm , H.-T. and Snatzke , G. 1979 . Tetrahedron Lett. , : 829
  • Sasaki , T. , Eguchi , S. and Toru , T. 1970 . J. Org. Chem. , 35 : 4109
  • Unfortunately, the solvolysis of 4(a)-(methylsulfonyloxy)ada-mantan-2-one (3a) has not been reported. However, as described later, even 4a requires 12 h at 25 °C to attain 20 half-lives in methanolysis. On the other hand, 3a is expected to react 10 times slower than 4a; Takeuchi, K., Ikai, K., Shibata, T., and Tsugeno, A., J. Org. Chem., 1988, 53, 2852. Therefore, the use of 3a appears to be impractical for synthetic purposes
  • Creary , X. and Geiger , C. C. 1983 . J. Am. Chem. Soc. , 105 : 7123
  • For a comparison, 4e gave 2e, 2a, and 6 in 3%, 54%, and 43%, respectively. 4e was prepared as an approximately 30(v/v)% solution in CH2Cl2 as described for the preparation of 4a: 13C NMR (22.5 MHz, CD2Cl2) δ 26.3, 32.4, 44.9, 52.4, 89.5 (CH); 29.6, 31.2, 33.7, 38.7 (CU2); 210.3 (C=0)
  • Fiord Lander , J. E. and Haky , J. E. 1981 . J. Am. Chem. Soc. , 103 : 1518
  • Cheung , C. K. , Tseng , L. T. , Lin , M.-H. , Srivastava , S. and le Noble , W. J. 1986 . J. Am. Chem. Soc. , 108 : 1598
  • Duddeck , H. and Wolff , P. 1977 . Org. Magn. Reson. , 9 : 528
  • Iidding , A. C. , Wynberg , H. and Strating , J. 1968 . Tetrahedron Lett. , : 5719
  • Numan , H. and Wynberg , H. 1978 . J. Org. Chem. , 43 : 2232

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.