Lewis and Brønsted basicity of phosphine-diazomethane derivatives. Issue 36 (28th August 2018)

• Record Type: Journal Article
• Authors: Schneider, Carolin; LaFortune, James H. W.; Melen, Rebecca L.; Stephan, Douglas W.
• Is Part Of: Dalton transactions. Volume 47:Issue 36(2018)
• Page Start: 12742
• Page End: 12749
• Publication Date: 2018-08-28
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c8dt02420k
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : The compounds EtOC(O)CHNN(PR3 ) (R = Ph1, Cy2, t Bu3 ) were prepared via the reactions of the diazomethane and a phosphine and their reactivity has been explored. Abstract : The compounds EtOC(O)CHNNPR3 (R = Ph1, Cy2, t Bu3 ) were prepared via the reactions of the diazomethane and a phosphine. In subsequent reactions with B(C6 F5 )3, the compounds2 and3 are shown to exhibit Lewis basicity at the carbonyl oxygen affording EtOC(O(B(C6 F5 )3 ))CHNNPR3 (R = Cy5, t Bu6 ). Reactions of5 and6 with water or phenol illustrated the Brønsted basicity at the nitrogen atom adjacent phosphorus, affording the compounds, [EtOC(O)CHNNHPR3 ][HOB(C6 F5 )3 ] (R = Cy7, t Bu8 ) and [EtOC(O)CHNNHPR3 ][PhOB(C6 F5 )3 ] (R = Cy9, t Bu10 ), respectively. The formulation of these products is confirmed via spectroscopic and crystallographic studies, and insight is garnered from computations.