The Arbuzov Reaction: Acylation of Phosphorus(III) Compounds

Author(s):  
A. Whitehead ◽  
S. R. Sieck ◽  
S. Mukherjee ◽  
P. R. Hanson
2017 ◽  
Vol 14 (6) ◽  
pp. 883-903 ◽  
Author(s):  
Boppudi Hari Babu ◽  
Gandavaram Syam Prasad ◽  
Chamarthi Naga Raju ◽  
Mandava Venkata Basaveswara Rao

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.


2019 ◽  
Vol 91 (1) ◽  
pp. 145-157 ◽  
Author(s):  
György Keglevich ◽  
Nóra Zsuzsa Kiss ◽  
Réka Henyecz ◽  
Zoltán Mucsi

AbstractThe usual advantage of microwave (MW) assistance is making organic reactions faster and more efficient. In this article we present reaction types from organophosphorus chemistry, when MW-assisted transformations (e.g. the direct esterification and alkylating esterification of phosphinic acids) may be promoted by suitable catalysts, or vice versa, when a catalytic reaction is enhanced by MW irradiation (e.g. the Arbuzov reaction of aryl halides), and when catalysts may be omitted or simplified under MW irradiation as shown by the alkylation of active methylene containing P=O substrates/the Kabachnik–Fields reaction/deoxygenation of phosphine oxides, and the Hirao reaction, respectively.


Author(s):  
N. P. Anoshina ◽  
�. I. Gol'dfarb ◽  
O. V. Voskresenskaya ◽  
P. A. Kirpichnikov ◽  
�. T. Mukmenev

1987 ◽  
Vol 16 (10) ◽  
pp. 1915-1918 ◽  
Author(s):  
Takayuki Kato ◽  
Kimiko Kobayashi ◽  
Shinji Masuda ◽  
Masahito Segi ◽  
Tadashi Nakajima ◽  
...  

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