The Preparation of Dimethyl α -Hydroxyphosphonates and the Chemical Shift Non-Equivalence of Their Diastereotopic Methyl Ester Groups

Hudson, H. R.; Yusuf, R. O.; Matthews, R. W.

doi:10.1080/10426500701690905

Cited by 40 publications

(11 citation statements)

References 18 publications

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“…A number of base-and acid-catalyzed, as well as different solid-salt-catalyzed methods were elaborated for the synthesis of -hydroxyphosphonates (Rá dai & Keglevich, 2018;Pudovik & Konovalova, 1979;Kharasch et al, 1960;Ruveda & De Licastro, 1972;Timmler & Kurz, 1971;Texierboullet & Foucard, 1980, 1982aHudson et al, 2008;Sardarian & Kaboudin, 1997;Smahi et al, 2008;Solhy et al, 2010;Kaboudin & Nazari, 2002). Thiourea-based organo-catalysts have also been used for the synthesis of tertiary -hydroxyphosphonates ISSN 2053ISSN -2296 # 2019 International Union of Crystallography (Kong et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

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The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

et al. 2019

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The crystal structures of seven -aryl--hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C 9 H 13 O 4 P, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, C 11 H 17 O 6 P, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, C 10 H 15 O 4 P, dimethyl [1-hydroxy-1-(4nitrophenyl)ethyl]phosphonate, C 10 H 14 NO 6 P, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, C 21 H 20 NO 6 P, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, C 21 H 20 ClO 4 P, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate, C 22 H 23 O 4 P, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C-OHÁ Á ÁO P chain-linked packing and the dimeric types of hydrogen-bond bridges of intermolecular pairs of such functions. The description is based on primary graph-set descriptors. Using graph-set descriptors one level deeper (i.e. secondary graph sets of the C-HÁ Á ÁO type) revealed a similarity in the graph-set descriptors, suggesting a fine interplay of substituent-and shape-dependent effects on strong-weak interactions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary C atom, but also by the nature and crowding of the ortho substituents of the -aryl group.

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Section: Introductionmentioning

confidence: 99%

“…31 Notes: (#) In this case, 0.3 equivalents of triethylamine was used. References: (a) Rowe & Spilling (2001); (b) Hudson et al (2008); (c) Rá dai et al (2018); (d) Pawar et al (2006); (e) Keglevich et al (2011); (f) Abramov (1952).…”

Section: Introductionmentioning

confidence: 99%

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

et al. 2019

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“…The Abramov reaction Scheme 8 Synthesis of α-hydroxyphosphonates using the Abramov reaction moderate to good yields [56]. This method can be convenient when the corresponding aldehyde is unavailable.…”

Section: Synthesis Of α-Hydroxyphosphonates and Related Compoundsmentioning

confidence: 99%

“…Recently, basic alumina (chromatographic grade) was found to catalyze efficiently the addition of dimethyl H-phosphonates to a variety of carbonyl compounds (aldehydes and ketones) at room temperature under solvent-free conditions (reaction time ca. 72 h) [56]. To speed-up the reaction, microwave irradiation (in combination with a strong base, DBN) [57] and ultrasound excitation [58] (in the presence K 2 HPO 4 as catalyst) were also used.…”

Section: Synthesis Of α-Hydroxyphosphonates and Related Compoundsmentioning

confidence: 99%

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

Sobkowski

Kraszewski

Stawiński

2014

Phosphorus Chemistry II

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This chapter provides an overview of recent advances in the development of new methods and protocols for the formation of the P-C bond using H-phosphonate diesters as starting materials. Various chemical and stereochemical aspects of the transition metal-catalyzed cross-coupling and organocatalyst-promoted reactions which are relevant to the synthesis of structurally diverse C-phosphonate derivatives are surveyed.

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“…The extract was washed with brine (30 mL), dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give a solid, which was recrystallized from ethyl acetate to afford pure α-hydroxyphosphonates 3. Sample 1 H, 13 C, and 31 P NMR spectra for 3a, 3h, and 3j are presented in the online Supplemental Materials (Figures S1-S9). …”

Section: General Procedures For the Synthesis Of Compounds 3a-3mmentioning

confidence: 99%

Convenient approach to synthesize tertiary α-hydroxy cyclic phosphonates catalyzed by potassium carbonate under solvent-free conditions

Wang

Zhou

Liu

et al. 2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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The Preparation of Dimethyl α -Hydroxyphosphonates and the Chemical Shift Non-Equivalence of Their Diastereotopic Methyl Ester Groups

Cited by 40 publications

References 18 publications

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

Convenient approach to synthesize tertiary α-hydroxy cyclic phosphonates catalyzed by potassium carbonate under solvent-free conditions

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