Lewis and Brønsted basicity of phosphine-diazomethane derivatives

Dalton Transactions : an International Journal of Inorganic Chemistry
Carolin SchneiderDouglas W Stephan

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.

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Citations

Apr 4, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Tyler A BartholomeCaleb D Martin
Aug 10, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Theodore A GazisRebecca L Melen
Sep 21, 2019·Chemical Communications : Chem Comm·Alina TrofimovaDouglas W Stephan
Dec 21, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Diya ZhuDouglas W Stephan
Jun 22, 2021·Chemical Communications : Chem Comm·Anthony WongGabriel Ménard
Jul 14, 2021·Chemical Communications : Chem Comm·Yunbo ZhaoDouglas W Stephan

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Methods Mentioned

BETA
NMR
X-ray

Software Mentioned

Gaussian
APEX
NBO
Bruker APEX - 2
SHELXTL
SHELX

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