The University of Southampton
University of Southampton Institutional Repository

Stereogenic properties of spiranes combined with one or two equivalent conventional centres of chirality

Coles, S.J., Davies, D.B., Hursthouse, M.B., Kilic, A., Sahin, S., Shaw, R.A. and Uslu, A. (2007) Stereogenic properties of spiranes combined with one or two equivalent conventional centres of chirality Journal of Organometallic Chemistry, 692, (13), pp. 2811-2821. (doi:10.1016/j.jorganchem.2007.02.003).

Record type: Article


Derivatives of the tri-spirane pentaerythritoxy-cyclophosphazene compound 1 have been used to investigate the stereogenic properties of spiranes combined with either one or two conventional centres of chirality. In compound 1, the two inner rings are carbocyclic and symmetrical and the two outer rings are cyclotriphosphazenes substituted in different positions to provide the conventional centres of chirality. Reaction of 1 in a 1:1 molar ratio with the unsymmetrical dinucleophilic reagent, 1,3-aminopropanol, gave the mono-spiro substituted derivative 2, which was shown to exist as a racemate by X-ray crystallography and 31P NMR spectroscopy on addition of a chiral solvating agent (CSA). Reaction of 1 with 1,3-aminopropanol in a 1:2 molar ratio gave three diastereoisomeric di-mono-spiro products 3a–3c, which were all shown to be racemates using a combination of X-ray crystallography (3a, 3c) and 31P NMR spectroscopy on addition of a CSA (3b), thus proving the case of the stereogenic properties of spirane molecules combined with two equivalent conventional centres of chirality. It is also shown by quantitative 31P NMR spectroscopy of the reaction mixture and by isolation of reaction products that the proportions of the diastereoisomers 3a:3b:3c are in approximate ratios of 1:2:1, respectively, and these results have been rationalised by analysis of the stereogenic properties of the series of reactions 1 ? 2 ? 3.

Full text not available from this repository.

More information

Published date: 2007
Keywords: trispiranes, phosphorus-nitrogen-compounds, p-31 nmr spectroscopy, aminoalcohols, derivatives, difunctional alcohols, x-ray crystallography, amines, cyclotriphosphazene derivatives, pentaerythritol, p-31, products, spiro, chiral solvating agent


Local EPrints ID: 54274
ISSN: 0022-328X
PURE UUID: a3a6b5cd-4b63-4642-8a52-c4c130f6b0fa
ORCID for S.J. Coles: ORCID iD

Catalogue record

Date deposited: 31 Jul 2008
Last modified: 17 Jul 2017 14:35

Export record



Author: S.J. Coles ORCID iD
Author: D.B. Davies
Author: M.B. Hursthouse
Author: A. Kilic
Author: S. Sahin
Author: R.A. Shaw
Author: A. Uslu

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton:

ePrints Soton supports OAI 2.0 with a base URL of

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.