Study of the Steric Structure of 7-Alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and Their Derivatives Using 1H NMR Spectroscopy |
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| Authors: | S G Klepikova V K Yu E E Fomicheva R D Mukhasheva K D Praliev V A Solomin K D Berlin |
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| Institution: | (1) Ministry of Education and Science for the Kazakhstan Republic, A. B. Bekturov Institute for Chemical Sciences, Almaty, 480100;(2) Chemistry Faculty, Oklahoma State University, Stillwater, 74078, USA |
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| Abstract: | Using the 1H NMR spectroscopic method it has been shown that 7-alkoxyalkyl-3-oxa-7-azabicyclo3.3.1]nonan-9-ones and 7-alkoxyalkyl-3-oxa-7-azabicyclo3.3.1]nonanes exist in deuterochloroform solution in a double chair conformation. 7-(3-Butoxypropyl)-3-oxa-7-azabicyclo3.3.1]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. |
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| Keywords: | 7-alkoxyalkyl-3-oxa-7-azabicyclo[3 3 1]nonan-9-one derivatives chair-boat chair-chair conformation structure 1H NMR |
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