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

Dalton Transactions : an International Journal of Inorganic Chemistry
Michael S HillStephen M Mansell

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(SiMe(3))(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 YCl(3) did not, however, yield the desired yttrium chloride complexes.

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Citations

Jan 15, 2016·Chemistry : a European Journal·Michael StollenzNattamai Bhuvanesh
Dec 22, 2010·Chemical Communications : Chem Comm·Paul BenndorfPeter W Roesky
May 22, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Aleksei O TolpyginAlexander A Trifonov
Nov 23, 2019·Chemistry : a European Journal·Robert Kretschmer
Sep 15, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Andreas RöschRobert Kretschmer
Oct 2, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Andreas RöschRobert Kretschmer
Apr 20, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Meng LiLixin Zhang
Sep 29, 2019·The Journal of Organic Chemistry·Connor O'DeaMichael Stollenz

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