STUDY OF THE STERIC STRUCTURE OF 7-ALKOXYALKYL-3-OXA-7-AZABICYCLO[3.3.1]NONAN-9-ONES AND THEIR DERIVATIVES USING <sup>1</sup>H NMR SPECTROSCOPY
Keywords:
7-alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one derivatives, chair-boat, chair-chair, conformation, structure, 1 H NMRAbstract
Using the 1H NMR spectroscopic method it has been shown that 7-alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and 7-alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonanes exist in deuterochloroform solution in a double chair conformation. 7-(3-Butoxypropyl)-3-oxa-7-azabicyclo[3.3.1]nonan-9-ol is a 1:1 mixture of the two stereoisomeric alcohols. One of them exists in a double chair conformation having an equatorial hydroxyl group with relation to the piperidine ring and the other in a chair-boat conformation having an axial hydroxyl group which involves an intramolecular hydrogen bond with the unshared electron pair of the nitrogen atom.
How to Cite
Klepikova, S. G.; Yu, V. K.; Fomicheva, E. E.; Mukhasheva, R. D.; Praliev, K. D.; Solomin, V. A.; Berlin, K. D. Chem. Heterocycl. Compd. 2003, 39, 1376. [Khim. Geterotsikl. Soedin. 2003, 1562.]
For this article in the English edition, see DOI 10.1023/B:COHC.0000010656.65900.72
