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Spontaneous resolution versus formation of racemic crystals of indenylpotassium complexes

Journal article
Authors Susanne Olsson
Anders Lennartson
Mikael Håkansson
Published in Journal of Organometallic Chemistry
Volume 741-742
Pages 131-135
ISSN 0022-328X
Publication year 2013
Published at Department of Chemistry and Molecular Biology
Pages 131-135
Language en
Links dx.doi.org/10.1016/j.jorganchem.201...
Keywords Organopotassium reagents, Asymmetric synthesis, Concomitant polymorphism, Spontaneous resolution
Subject categories Inorganic Chemistry

Abstract

During a study of stereochemically labile organometallic reagents, we found that crystallisation of [K(ind)(pmdta)](n) (ind = indenyl, pmdta = N,N,N',N '',N ''-pentamethyldiethylenetriamine) from tetrahydrofuran (THF) gave rise to three different crystalline phases depending on the concentration. The more concentrated solutions gave racemic crystals of the previously known coordination polymer [K(ind)(pmdta)](n), alpha-1. More dilute solutions gave crystals of a new phase, beta-1, which was found to undergo spontaneous resolution. From even more dilute solutions, we were able to isolate a chiral inclusion compound with THF, 2, which also undergoes spontaneous resolution. Crystals of beta-1 and 2 were enantiomerically pure, and since beta-1 is a reactive organometallic reagent, attempts were made to use the crystals in enantioselective synthesis. Reacting single crystals with N-chlorosuccinimide gave rise to chiral 1-chloroindene, but no enantiomeric excess was observed.

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