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- W4384927144 abstract "Secondary phosphine oxides R2P(O)H are a relatively stable tautomeric form of secondary phosphinous acids R2P–OH that with imine/iminium species, or their donors, form compounds with a P(O)–Csp3–N linkage (the phospha-Mannich reaction). These can be referred to as (α-aminoalkyl)phosphine oxides, (α-phosphinoylalkyl)amines, or P(O),N-acetals. Compared to P–Csp3–N linkages of P,N-acetals, products of phospha-Mannich reactions involving secondary phosphines R2PH, the P(O)–Csp3–N linkage is significantly more stable that allows for many examples of α-functionalized P(O),N-acetals and α-phosphinoylated N-heterocycles, whereas such examples for P,N-acetals are rare. Trivalent derivatives of phosphinous acids such as halides R2P–Hal, esters R2P–OR’ (phosphinites), amides R2P–NR’2 (aminophosphines), and phosphides R2P–PR’2 (biphosphines) also participate in Mannich-type reactions with mechanisms depending on the reactants. The phosphinous halides and esters react with (α-alkoxyalkyl)amines (N,O-acetals) and (α-haloalkyl)amines (N,Hal-acetals), respectively, via Arbuzov-type intermediates that are rearranged into P(O),N-acetals and alkyl halides (Arbuzov rearrangement). Furthermore, unlike phospha-Mannich reactions involving phosphines, secondary phosphine oxides and P(O),N-acetals are less sensitive to oxidation, and imines/iminium species can be generated not only under conventional Mannich conditions, i.e., from N,E-acetals (E = OH, O, N, halogen, etc.), but also, for example, by oxidation of α-C-atom of amines, or by oxidation of alcohols to aldehydes that than form imines/iminium species with amines." @default.
- W4384927144 created "2023-07-22" @default.
- W4384927144 creator A5059696943 @default.
- W4384927144 date "2023-07-20" @default.
- W4384927144 modified "2023-09-25" @default.
- W4384927144 title "Phospha-Mannich reactions of phosphinous acids R<sub>2</sub>P–OH and their derivatives" @default.
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