A Simple, Efficient Synthesis of Dibenzyl and Di-<i>p</i>-nitrobenzyl 1-Hydroxyalkanephosphonates
作者:Maria Hoffmann
DOI:10.1055/s-1988-33434
日期:——
Dibenzyl and di-p-nitrobenzyl 1-hydroxyalkanephosphonates 3a-i are prepared by alkylation of 1-hydroxyalkanephosphonic acids 1 with O-benzyl and O-(p-nitrobenzyl)-N,N′-dicyclohexylisoureas 2.
Deamination of 1-Aminoalkylphosphonic Acids: Reaction Intermediates and Selectivity
作者:Anna Brol、Tomasz K. Olszewski
DOI:10.3390/molecules27248849
日期:——
acids in the reaction with HNO2 (generated "in situ" from NaNO2) yields a mixture of substitution products (1-hydroxyalkylphosphonic acids), elimination products (vinylphosphonic acid derivatives), rearrangement and substitution products (2-hydroxylkylphosphonic acids) as well as H3PO4. The variety of formed reaction products suggests that 1-phosphonoalkylium ions may be intermediates in such deamination
Reactions of Chiral Phosphorous Acid Diamides: The Asymmetric Synthesis of Chiral .alpha.-Hydroxy Phosphonamides, Phosphonates, and Phosphonic Acids
作者:Vincent J. Blazis、Kevin J. Koeller、Christopher D. Spilling
DOI:10.1021/jo00109a025
日期:1995.2
Addition of aldehydes to the anions of chiral phosphorous acid diamides in THF solution gave a-hydroxy phosphonamides in good yield. The diastereoselectivity was strongly dependent upon the diamide used and ranged from poor to good. The phosphorous acid diamides 2a and 2b (R(1) = -(CH2)4-,R(2) = CH(2)Ph and CH(2)CMe(3), respectively) gave the best selectivity, and their reactions with a range of aldehydes were studied. Diamide 2b consistently gave good selectivities, whereas diamide 2a was only moderately selective. Aromatic, aliphatic, and unsaturated aldehydes are tolerated under the reaction conditions. The phosphonamides were hydrolyzed with aqueous HCl in dioxane to give a-hydroxy phosphonic acids. While direct methanolysis of the phosphonamides was unsuccessful, methylation of the phosphonic acids with diazomethane gave alpha-hydroxy dimethylphosphonates.
Kuskow et al., Doklady Akademii Nauk SSSR, 1958, vol. 120, p. 786
作者:Kuskow et al.
DOI:——
日期:——
Hoffmann, Maria, Polish Journal of Chemistry, 1982, vol. 56, # 7/8/9, p. 1191 - 1194