Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 36, 2018
Previous Article Next Article

Lewis and Brønsted basicity of phosphine-diazomethane derivatives

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

Article information


Submitted
12 Jun 2018
Accepted
14 Aug 2018
First published
15 Aug 2018

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

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

Social activity

Search articles by author

Spotlight

Advertisements