Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives.

Abstract:

:The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled (31)P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:1 ratio, consistent with formation of diastereoisomers. The meso and racemic forms of compound 2 were separated by column chromatography on silica gel and characterised by elemental analysis, mass spectrometry, (31)P NMR spectroscopy, and X-ray crystallography. Using HPLC with a chiral stationary phase, the racemic form of compound 2 was further separated into enantiomers, which were characterised by circular dichroism (CD) spectroscopy. This is the first report of the separation of enantiomers in the field of cyclophosphazene chemistry and hence the first CD spectra of derivatives in which the cyclophosphazene ring is at the chiral centre.

journal_name

Chirality

journal_title

Chirality

authors

Bui TT,Coles SJ,Davies DB,Drake AF,Eaton RJ,Hursthouse MB,Kiliç A,Shaw RA,Yeşilot S

doi

10.1002/chir.20187

subject

Has Abstract

pub_date

2005-10-01 00:00:00

pages

438-43

issue

8

eissn

0899-0042

issn

1520-636X

journal_volume

17

pub_type

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