A novel ring closure in the Michaelis–Arbuzov reaction of trialkyl phosphites with phthaloyl chloride

1967 ◽  
Vol 0 (20) ◽  
pp. 1060-1061 ◽  
Author(s):  
K. Darrell Berlin ◽  
Donald H. Burpo ◽  
Roland U. Pagilagan ◽  
Duane Bude
Keyword(s):  
Ring Closure ◽  
Arbuzov Reaction ◽  
Trialkyl Phosphites

Visible-Light Photo-Arbuzov Reaction of Aryl Bromides and Trialkyl Phosphites Yielding Aryl Phosphonates

ACS Catalysis ◽  
2016 ◽  
Vol 6 (12) ◽  
pp. 8410-8414 ◽  
Author(s):  
Rizwan S. Shaikh ◽  
Simon J. S. Düsel ◽  
Burkhard König
Keyword(s):  
Visible Light ◽  
Arbuzov Reaction ◽  
Aryl Bromides ◽  
Trialkyl Phosphites

scholarly journals Regioselective O/C phosphorylation of α-chloroketones: a general method for the synthesis of enol phosphates and β-ketophosphonates via Perkow/Arbuzov reaction

RSC Advances ◽  
2020 ◽  
Vol 10 (49) ◽  
pp. 29493-29497
Author(s):  
Yuepeng Cao ◽  
Zhenhua Gao ◽  
Junchen Li ◽  
Xiaojing Bi ◽  
Ling Yuan ◽  
...  
Keyword(s):  
Arbuzov Reaction ◽  
Trialkyl Phosphites ◽  
General Method

A highly regioselective O/C phosphorylation of α-chloroketones with trialkyl phosphites was developed in the preparation of enol phosphates and β-ketophosphonates.

Ring Closure Matrix

2015 ◽  
Vol 19 (3) ◽  
pp. 274-281
Author(s):  
Milan Randic ◽  
Marjana Novic ◽  
Dejan Plavsic
Keyword(s):  
Ring Closure

Synthesis of Phosphonates via Michaelis-Arbuzov Reaction

2017 ◽  
Vol 14 (6) ◽  
pp. 883-903 ◽  
Author(s):  
Boppudi Hari Babu ◽  
Gandavaram Syam Prasad ◽  
Chamarthi Naga Raju ◽  
Mandava Venkata Basaveswara Rao
Keyword(s):  
Reaction Times ◽  
Biologically Active ◽  
Fine Tuning ◽  
Arbuzov Reaction ◽  
Reaction Conditions ◽  
Solvent Type ◽  
Potential Applications ◽  
Synthetic Methodologies ◽  
Optimal Reaction ◽  
The Arbuzov Reaction

Background: Michaelis–Arbuzov reaction has played a key role for the synthesis of dialkyl or diaryl phosphonates by reacting various alkyl or aryl halides with trialkyl or triaryl phosphite. This reaction is very versatile in the formation of P-C bond from the reaction of aliphatic halides with phosphinites or phosphites to yield phosphonates, phosphinates, phosphine oxides. The Arbuzov reaction developed some methodologies, possible mechanistic pathways, selectivity, potential applications and biologically active various phosphonates. Objective: The synthesis of phosphonates via Michaelis–Arbuzov reaction with many new and fascinating methodologies were developed and disclosed in the literature, and these are explored in this review. Conclusion: This review has discussed past developments and vast potential applications of Arbuzov reaction in the synthesis of organophosphonates. As presented in this review, various synthetic methodologies were developed to prepare a large variety of phosphonates. Improvements in the reaction conditions of Lewis-acid mediated Arbuzov rearrangement as well as the development of MW-assisted Arbuzov rearrangement were discussed. Finally, to achieve high selectivities and yields, fine-tuning of reaction conditions including solvent type, temperature, and optimal reaction times to be considered.

A new heterocyclic ring closure in ferricyanide oxidation of 2,4,6-triphenylpyridinium salts

1983 ◽  
Vol 48 (11) ◽  
pp. 3307-3314 ◽  
Author(s):  
Petr Nesvadba ◽  
Petr Štrop ◽  
Josef Kuthan
Keyword(s):  
Alkaline Solution ◽  
Heterocyclic Ring ◽  
Potassium Ferricyanide ◽  
Probable Mechanism ◽  
Ring Closure ◽  
Pyridinium Salts ◽  
Mechanism Of Formation ◽  
Pyrrole Derivatives ◽  
Quaternary Pyridinium Salts ◽  
Heterocyclic Derivatives

The quaternary pyridinium salts Ia-Ic react with alkaline solution of potassium ferricyanide to give the condensed heterocyclic derivatives IIIa, b, IV, whereas the salts Id-If give the pyrrole derivatives IIa-IIc under the same conditions. The diaza heterocycle IIIa reacts with methyl iodide to give methoiodide V, whereas by action of bromine it produces two monobromo derivatives VIa, b. The pyrrole derivatives IIa, b give monobromo derivatives IId, e on bromination. A probable mechanism of formation of the heterocyclic derivatives is discussed.

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