Issue 1, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2011
Accepted
16 Aug 2011
First published
08 Sep 2011

Dalton Trans., 2012,41, 237-242

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements