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Stereogenic properties of spiranes combined with four equivalent conventional centres of chirality

Stereogenic properties of spiranes combined with four equivalent conventional centres of chirality
Stereogenic properties of spiranes combined with four equivalent conventional centres of chirality
Derivatives of the tri-spirane pentaerythritoxy-cyclophosphazene compound, 1, have been used to investigate the stereogenic properties of spiranes combined with four equivalent 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. The case of combining spiranes with four equivalent centres of chirality has been investigated by the reaction of 1 with dimethylamine in a 1 : 8 molar ratio to give four diastereoisomeric products, in which the two cyclophosphazene rings are non-geminally di-substituted in either cis or trans configurations; viz. the cis–cis ( 2a), cis–trans ( 2b) and two trans–trans substituted dimethylamine derivatives 2c and 2d. The structure and stereogenic properties of compound 2a (C2 symmetry) have been characterized previously by both X-ray crystallography and 31P NMR spectroscopy on addition of a chiral solvating agent (CSA) and the structures and stereogenic properties of compounds 2b (C1) and 2d (C2) have been similarly characterized in this work. The structure of compound 2c has been characterised by X-ray crystallography and found to be meso with the relatively rare S4 symmetry. The four diastereoisomeric products 2a–2d represent all the possible stereochemical isomers of a spirane combined with four equivalent conventional centres of chirality.
pentaerythritol, stereochemistry, configurations, hexachlorocyclotriphosphazatriene, spiro, cyclotriphosphazenes, phosphorus-nitrogen compounds, derivatives, phosphazenes, helical chirality
1477-9226
2040-2047
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kılıç, Adem
565a42ec-2d18-4142-8b37-bb74b244b2f5
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kılıç, Adem
565a42ec-2d18-4142-8b37-bb74b244b2f5
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87

Coles, Simon J., Davies, David B., Eaton, Robert J., Hursthouse, Michael B., Kılıç, Adem, Shaw, Robert A. and Uslu, Aylin (2007) Stereogenic properties of spiranes combined with four equivalent conventional centres of chirality. Dalton Transactions, (20), 2040-2047. (doi:10.1039/b700464h).

Record type: Article

Abstract

Derivatives of the tri-spirane pentaerythritoxy-cyclophosphazene compound, 1, have been used to investigate the stereogenic properties of spiranes combined with four equivalent 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. The case of combining spiranes with four equivalent centres of chirality has been investigated by the reaction of 1 with dimethylamine in a 1 : 8 molar ratio to give four diastereoisomeric products, in which the two cyclophosphazene rings are non-geminally di-substituted in either cis or trans configurations; viz. the cis–cis ( 2a), cis–trans ( 2b) and two trans–trans substituted dimethylamine derivatives 2c and 2d. The structure and stereogenic properties of compound 2a (C2 symmetry) have been characterized previously by both X-ray crystallography and 31P NMR spectroscopy on addition of a chiral solvating agent (CSA) and the structures and stereogenic properties of compounds 2b (C1) and 2d (C2) have been similarly characterized in this work. The structure of compound 2c has been characterised by X-ray crystallography and found to be meso with the relatively rare S4 symmetry. The four diastereoisomeric products 2a–2d represent all the possible stereochemical isomers of a spirane combined with four equivalent conventional centres of chirality.

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More information

Published date: 2007
Keywords: pentaerythritol, stereochemistry, configurations, hexachlorocyclotriphosphazatriene, spiro, cyclotriphosphazenes, phosphorus-nitrogen compounds, derivatives, phosphazenes, helical chirality

Identifiers

Local EPrints ID: 54271
URI: https://eprints.soton.ac.uk/id/eprint/54271
ISSN: 1477-9226
PURE UUID: 0c638206-b562-42af-80d8-7623d20297d0
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 30 Jul 2008
Last modified: 20 Jul 2019 01:09

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