Issue 9, 2009
From the journal:

CrystEngComm

Network analysis of bicyclo[3.3.1]nonanes: the diol, the dione and the acetal†

Carl-Johan Wallentin,a   Edvinas Orentas,b   Magnus T. Johnson,a   Eugenijus Butkus,*b   Ola F. Wendt,*a   Lars Öhrström*c  and  Kenneth Wärnmark*a  

* Corresponding authors

a Organic Chemistry, Department of Chemistry, Lund University, P. O. Box 124, Lund, Sweden
E-mail: ola.wendt@organic.lu.se, Carl-Johan.Wallentin@organic.lu.se, Kenneth.Warnmark@organic.lu.se
Fax: +46 46 2228209
Tel: +46 46 222 0000

b Dept Organic Chemistry, Naugarduko 24, Vilnius, Lithuania
E-mail: edvinas.orentas@chf.vu.lt, Eugenijus.Butkus@chf.vu.lt
Fax: +370-5-2330987
Tel: +370-682-63092

c Dept. of Chemical and Biological Engineering, Chalmers University of Technology, Göteborg, Sweden
E-mail: ohrstrom@chalmers.se
Fax: +46 31 772 3858

Abstract

The solid state structure of endo,endo-bicyclo[3.3.1]nonane-2,6-diol, rac-2, shows a hydrogen bonded, three-connected, chiral 3D-net with utg-topology, distinctively different from those formed by the so called tubuland diols, e.g.2,6-dimethylbicyclo[3.3.1]nonane-exo-2,exo-6-diol, rac-5, that crystallise as three-connected, chiral eta-nets and from the qtz-net formed by weaker hydrogen bonds in the bicyclo[3.3.1]nonane-2,6-dione, 3. The protected bicyclo[3.3.1]nonane-2,6-dione, bis-2,6-ethylenedioxy acetal, 4, has a structure governed by weaker forces and can be interpreted as close packed stacks.

Graphical abstract: Network analysis of bicyclo[3.3.1]nonanes: the diol, the dione and the acetal

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Article information

DOI
https://doi.org/10.1039/B905122H
Article type
Communication
Submitted
12 Mar 2009
Accepted
16 Jun 2009
First published
07 Jul 2009

CrystEngComm, 2009,11, 1837-1841

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Network analysis of bicyclo[3.3.1]nonanes: the diol, the dione and the acetal

C. Wallentin, E. Orentas, M. T. Johnson, E. Butkus, O. F. Wendt, L. Öhrström and K. Wärnmark, CrystEngComm, 2009, 11, 1837 DOI: 10.1039/B905122H

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