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

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.

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Citation

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).

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

Identifiers

Local EPrints ID: 54274
URI: http://eprints.soton.ac.uk/id/eprint/54274
ISSN: 0022-328X
PURE UUID: a3a6b5cd-4b63-4642-8a52-c4c130f6b0fa
ORCID for S.J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

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

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Contributors

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

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