Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 3
17
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

On the Stereochemistry of Bicyclo[n.2.0]Alkanediols

, &
Pages 201-204 | Received 04 Apr 1973, Published online: 06 Dec 2006

References

  • Harding , K. E. , Trotter , J. W. and May , L. 1972 . Synthetic Commun. , 2 : 231
  • Paukstelis , J. V. and Kao , J. 1972 . J. Amer. Chem. Soc. , 94 : 4783
  • Paukstelis , J. V. and Kao , J. unpublished results. Private communication from Prof. J. V. Paukstelis
  • The infrared spectrum of this diol was identical with the spectrum of authentic material prepared in another manner by Paukstelis and Kao.2,3
  • All melting points were determined using an open capillary
  • The original assignment of cis stereochemistry to the diols obtained by direct hydride reduction of ketoacetates 6 and 8 was based only on indirect evidence. We have now shown that the infrared spectra of both the cis and the trans hydroxyacetate obtained by reduction of ketoacetate 8 exhibit hydrogen-bonding O-H absorption. The work of Paukstelis2,3 has established unequivocally that the diols obtained by direct reduction of ketoacetates 6 and 8 are trans-diols and that the diols described in this paper are cis-diols

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.