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Chasing an Elusive Alkoxide: Attempts to Synthesize [OC(tBu)(CF3)2]

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Abstract:

The synthesis of the alkoxide [OC(tBu)(CF3)2] by the reaction of tBuM-reagents (M = Li; MgX) with hexafluoroacetone was attempted. This alkoxide was anticipated to be a good building block for novel weakly coordinating anions. However, in all attempted syntheses – also supported by theoretical DFT calculations – it was shown that [H] addition is favored over [tBu] addition. Thus compounds like [(Li(OC(H)(CF3)2]4·2Et2O (1) and (CF3)2(H)COMgCl·(OEt2)2 (4) were formed. An unexpected result was the formation of (THF)3LiO(CF3)2OC(H)(CF3)2(2), an addition compound built from [(CF3)2C(H)O] and hexafluoroacetone. The alkoxy-alkoxide 2 could be useful for further applications.

Keywords: ALKOXIDE; DFT; WEAKLY COORDINATING ANION (WCA)

Document Type: Miscellaneous

DOI: http://dx.doi.org/10.2533/000942906777674822

Publication date: April 1, 2006

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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