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Issue 2, 2014
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The frustrated Lewis pair pathway to methylene phosphonium systems

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Abstract

Reaction of HB(C6F5)2 with (tBu3C6H2)P(vinyl)2 does not yield the expected ethylene-bridged frustrated Lewis pair (FLP) but its cyclic methylene phosphonium isomer which is formed in a unique way by subsequent internal 1,2-P/B addition to the vinylphosphane unit. The product is a rare example of a stable phosphorus analogue of the ubiquitous iminium salts. It features a short P[double bond, length as m-dash]C bond (1.637(3) Å). Subsequent reactions with pyridine and with dihydrogen probably proceed by equilibration with the “invisible” ethylene-bridged FLP isomer. The reaction of (tBu3C6H2)P(vinyl)2 with B(C6F5)3 gave the zwitterionic acyclic methylene phosphonium product that was crystallized at low temperature and isolated. The X-ray crystal structure analysis also revealed a short P[double bond, length as m-dash]C bond (1.635(5) Å).

Graphical abstract: The frustrated Lewis pair pathway to methylene phosphonium systems

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Article information


Submitted
20 Aug 2013
Accepted
24 Oct 2013
First published
06 Dec 2013

Chem. Sci., 2014,5, 797-803
Article type
Edge Article

The frustrated Lewis pair pathway to methylene phosphonium systems

Y. Hasegawa, G. Kehr, S. Ehrlich, S. Grimme, C. G. Daniliuc and G. Erker, Chem. Sci., 2014, 5, 797
DOI: 10.1039/C3SC52327F

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