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Issue 12, 2006
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Racemic N-aryl bis(amidines) and bis(amidinates): on the trail of enantioselective organolanthanide catalysts

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Abstract

A series of racemic N-aryl-substituted trans-1,2-diaminocyclohexyl (t-1,2-DACH)-linked bis(amidines) were synthesised and their solution behaviour, and solid-state structures were investigated. The amidine functionalities within these compounds were extremely sterically hindered, with ortho-aryl substitution found to hinder N–Ar bond rotation. The results of these studies were used to rationalise the lack of reactivity of these compounds with [Y{N(SiMe3)2}3]. Dilithiation of the t-1,2-DACH linked bis(amidines) did, however, proceed easily and the solution behaviour and solid-state structures of the resulting THF-solvated lithium amidinates were investigated. All the compounds showed similar structures in the solid-state, while NMR experiments indicated that the solid-state structures were likely to be maintained in solution. Attempted metathesis reactions with YCl3 did not, however, yield the desired yttrium chloride complexes.

Graphical abstract: Racemic N-aryl bis(amidines) and bis(amidinates): on the trail of enantioselective organolanthanide catalysts

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Supplementary files

Article information


Submitted
23 Sep 2005
Accepted
23 Nov 2005
First published
09 Dec 2005

Dalton Trans., 2006, 1544-1553
Article type
Paper

Racemic N-aryl bis(amidines) and bis(amidinates): on the trail of enantioselective organolanthanide catalysts

M. S. Hill, P. B. Hitchcock and S. M. Mansell, Dalton Trans., 2006, 1544
DOI: 10.1039/B513521D

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