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Spontaneous resolution versus formation of racemic crystals of indenylpotassium complexes

Susanne Olsson ; Anders Lennartson (Institutionen för kemi- och bioteknik, Polymerteknologi) ; Mikael Håkansson
Journal of Organometallic Chemistry (0022-328X). Vol. 741-742 (2013), p. 131-135.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: Organopotassium reagents, Asymmetric synthesis, Concomitant polymorphism, Spontaneous resolution

Denna post skapades 2013-09-10. Senast ändrad 2016-08-22.
CPL Pubid: 182963


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Institutioner (Chalmers)

Institutionen för kemi och molekylärbiologi (GU)
Institutionen för kemi- och bioteknik, Polymerteknologi (2005-2014)


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