NMR studies of the bishydroxy bisphosphonate synthesis from o‐phthalic aldehyde and diethyl phosphite

Abstract

ABSTRACT:

(Dimethoxyphosphoryl)(phenyl)methyl benzoate

“…The title compound, (I), was synthesized for a study of its antimicrobial activity against Bacillus subtilis. The hydroxyphosphonic acid derivative was found to have moderate antimicrobial activity (inhibition zone = 7.5 mm), The crystal packing is stabilized by van der Waals forces, and bond lengths and angles in (I) are in agreement with the values reported in the literature (Smaardijk et al, 1985;Deron et al, 2002).…”

Synthesis of 1,2-oxaphosphinane 2-oxides and 1,2-oxaphosphinine 2-oxides: δ-phosphonolactones and δ-phosphinolactones

“…Similarly, the nucleophilic adduct of benzene-1,2-dicarbaldehyde and diethyl phosphite underwent transesterification to afford stereomeric 1-diethoxyphosphoryl-3-ethoxy-4-hydroxybenzo[d][1,2]oxaphosphinine 2-oxide. 16 The acid-catalyzed transesterification is an alternative and efficient method for the synthesis of 1,2-oxaphosphinane 2-oxides. 2-Hydroxy-3,4-dihydrobenzo[e][1,2]oxaphosphinine 2-oxide was synthesized in 90% yield from diethyl(2-hydroxyphenethyl)phosphonate with p-TsOH as catalyst in refluxing xylene and was further transformed to a hapten to generate a catalytic antibody that cleaved the amide bond in nucleophilic catalysis (Scheme 4).…”

“…Similarly, the nucleophilic adduct of benzene-1,2-dicarbaldehyde and diethyl phosphite underwent transesterification to afford stereomeric 1-diethoxyphosphoryl-3-ethoxy-4-hydroxybenzo[ d ][1,2]oxaphosphinine 2-oxide. 16…”

Weak Hydrogen Bond in Cl3CH· · ·O═P(n-Bu)3

“…4,5 The phosphoroorganic compounds such as phoshine oxide, phosphinate, phosphonate, and phosphate have a highly polarized phosphoryl oxygen atom P O facile for the formation of hydrogen bonds via intra-and intermolecular interactions, the strength of which depends on atoms around phosphorus atom. The P O interaction with H O and H N groups usually forms strong hydrogen bonds [6][7][8][9][10] and is the most popular interaction found in many phosphoryl compounds. These hydrogen bonds determine the conformational preferences in hydroxyphosphonates and aminophosphonates in solution and in crystal networks, 10,11 and is important in transferring spinspin interaction.…”