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Issue 25, 2011
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Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs

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Abstract

While B(C6F5)3 forms the adducts (CH2)4CO2B(C6F5)31 and (CHMeCO2)2B(C6F5)37 with δ-valerolactone and lactide, the frustrated Lewis pairs derived from B(C6F5)3 and phosphine or N-bases react with lactone to effect ring opening affording zwitterionic species of the form L(CH2)4CO2B(C6F5)3 (L = tBu3P 2, Cy3P 3, C5H3Me3N 4, PhNMe2 5, C5H6Me4NH 6) while reaction with rac-lactide results in ring contraction to give salts [LH][OCCHMeCO2(CMe)OB(C6F5)3] (L = tBu3P 8, Cy3P 9, C5H3Me2N 10, C5H6Me4NH 11). The mechanistic implications of these reactions are discussed.

Graphical abstract: Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs

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Publication details

The article was received on 17 Mar 2011, accepted on 26 Apr 2011 and first published on 25 May 2011


Article type: Paper
DOI: 10.1039/C1DT10449G
Citation: Dalton Trans., 2011,40, 6771-6777
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    Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs

    C. Kreitner, S. J. Geier, L. J. E. Stanlake, C. B. Caputo and D. W. Stephan, Dalton Trans., 2011, 40, 6771
    DOI: 10.1039/C1DT10449G

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