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Issue 36, 2018
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Lewis and Brønsted basicity of phosphine-diazomethane derivatives

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The compounds EtOC([double bond, length as m-dash]O)CHNNPR3 (R = Ph 1, Cy 2, tBu 3) were prepared via the reactions of the diazomethane and a phosphine. In subsequent reactions with B(C6F5)3, the compounds 2 and 3 are shown to exhibit Lewis basicity at the carbonyl oxygen affording EtOC([double bond, length as m-dash]O(B(C6F5)3))CHNNPR3 (R = Cy 5, tBu 6). Reactions of 5 and 6 with water or phenol illustrated the Brønsted basicity at the nitrogen atom adjacent phosphorus, affording the compounds, [EtOC([double bond, length as m-dash]O)CHNNHPR3][HOB(C6F5)3] (R = Cy 7, tBu 8) and [EtOC([double bond, length as m-dash]O)CHNNHPR3][PhOB(C6F5)3] (R = Cy 9, tBu 10), respectively. The formulation of these products is confirmed via spectroscopic and crystallographic studies, and insight is garnered from computations.

Graphical abstract: Lewis and Brønsted basicity of phosphine-diazomethane derivatives

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Supplementary files

Article information

12 Jun 2018
14 Aug 2018
First published
15 Aug 2018

Dalton Trans., 2018,47, 12742-12749
Article type

Lewis and Brønsted basicity of phosphine-diazomethane derivatives

C. Schneider, J. H. W. LaFortune, R. L. Melen and D. W. Stephan, Dalton Trans., 2018, 47, 12742
DOI: 10.1039/C8DT02420K

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