Issue 20, 2000
From the journal:

Journal of the Chemical Society, Dalton Transactions

Synthesis of chiral organotin hydrides containing menthyl and oxazoline substituents †

Dainis Dakternieks,*a   Kerri Dunn,a   Carl H. Schiesserb  and  Edward R. T. Tiekinkc  

* Corresponding authors

a Centre for Chiral and Molecular Technologies, Deakin University, Geelong, Victoria, Australia

b School of Chemistry, The University of Melbourne, Victoria, Australia

c Department of Chemistry, The University of Adelaide, South Australia, Australia

Abstract

A series of chiral non-racemic triorganotin halides and triorganotin hydrides containing one or two (1R,2S,5R)-menthyl (Men) substituents as well as 2-(4,4-dimethyl-2-oxazolinyl)-5-(methyl)phenyl (L) or chiral 2-(4-isopropyl-2-oxazolinyl)-5-(methyl)phenyl ligand (L*) have been synthesized and characterised. Each of SnCl(Men)PhL and SnH(Men)PhL has a stereogenic tin centre and were isolated in diastereomeric ratios of 70∶30 and 50∶50, respectively; SnCl(Men)PhL* and SnH(Men)PhL* were synthesized in diastereomeric ratios of 50∶50 and 66∶34, respectively. Single crystal X-ray analysis of SnCl(Men)2L and SnCl(Men)PhL reveals a tendency towards five co-ordination at the tin centre as a result of N→Sn interactions. AM1 calculations provide good qualitative predictability of the molecular geometries observed in the solid state as well as the diastereomeric ratios in solution.

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B004259P
Article type
Paper
Submitted
30 May 2000
Accepted
07 Sep 2000
First published
02 Oct 2000

J. Chem. Soc., Dalton Trans., 2000, 3693-3698

Permissions

Request permissions

Synthesis of chiral organotin hydrides containing menthyl and oxazoline substituents

D. Dakternieks, K. Dunn, C. H. Schiesser and E. R. T. Tiekink, J. Chem. Soc., Dalton Trans., 2000, 3693 DOI: 10.1039/B004259P

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements