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Issue 1, 2012
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Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to alkynes

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Abstract

The reaction of tBu(C6H4O2)P, with the borane B(C6F5)3 gives rise to NMR data consistent with the formation of the classical Lewis acid–base adduct tBu(C6H4O2)P(B(C6F5)3) (1). In contrast, the NMR data for the corresponding reactions of tBu(C20H12O2)P and Cl(C20H12O2)P with B(C6F5)3 were consistent with the presence of equilibria between free phosphine and borane and the corresponding adducts. Nonetheless, in each case, the adducts tBu(C20H12O2)P(B(C6F5)3) (2) and Cl(C20H12O2)P(B(C6F5)3) (3) were isolable. The species 1 reacts with PhCCH to give the new species tBu(C6H4O2)P(Ph)C[double bond, length as m-dash]CHB(C6F5)3 (4) in near quantitative yield. In an analogous fashion, the addition of PhCCH to solutions of the phosphinestBu(C20H12O2)P, tBuPCl2 and (C6H3(2,4-tBu2)O)3P each with an equivalent of B(C6F5)3 gave rise to L(Ph)C[double bond, length as m-dash]CHB(C6F5)3 (L = tBu(C20H12O2)P5, tBuPCl26 and (C6H3(2,4-tBu2)O)3P 7). X-Ray data for 1, 2, 6 and 7 are presented. The implications of these findings are considered.

Graphical abstract: Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to alkynes

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Publication details

The article was received on 23 Jun 2011, accepted on 16 Aug 2011 and first published on 08 Sep 2011


Article type: Paper
DOI: 10.1039/C1DT11196E
Citation: Dalton Trans., 2012,41, 237-242
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    Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to alkynes

    C. B. Caputo, S. J. Geier, E. Y. Ouyang, C. Kreitner and D. W. Stephan, Dalton Trans., 2012, 41, 237
    DOI: 10.1039/C1DT11196E

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