Nucleophilic substitution at acetylenic carbon. Kinetics and mechanism of the Arbuzov reaction of substituted phenylbromo-and phenylchloroacetylenes with triethyl phosphite

1971 ◽  
Vol 93 (15) ◽  
pp. 3694-3700 ◽  
Author(s):  
Sidney I. Miller ◽  
Atsushi Fujii
Keyword(s):  
Nucleophilic Substitution ◽  
Triethyl Phosphite ◽  
Kinetics And Mechanism ◽  
Arbuzov Reaction ◽  
The Arbuzov Reaction

The arbuzov reaction of triethyl phosphite with elemental iodine

1980 ◽  
Vol 21 (3) ◽  
pp. 321-322 ◽  
Author(s):  
A. Skowrońska ◽  
M. Pakulski ◽  
J. Michalski ◽  
D. Cooper ◽  
S. Trippett
Keyword(s):  
Triethyl Phosphite ◽  
Arbuzov Reaction ◽  
The Arbuzov Reaction ◽  
Elemental Iodine

Use of 5-deoxy-ribo-hexofuranose derivatives for the preparation of 5'-nucleotide phosphonates and homoribonucleosides

1989 ◽  
Vol 54 (4) ◽  
pp. 1055-1066 ◽  
Author(s):  
Sergei N. Mikhailov ◽  
Nelly Sh. Padyukova ◽  
Marat Ya. Karpeiskii ◽  
Lidiya I. Kolobushkina ◽  
Leon N. Beigelman
Keyword(s):  
Triethyl Phosphite ◽  
Arbuzov Reaction ◽  
Trimethylsilyl Derivatives ◽  
The Arbuzov Reaction ◽  
General Method

A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose which can easily be produced in preparative quantities from D-glucose. Phosphonate IIIe was synthesized by means of the Arbuzov reaction between 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and triethyl phosphite. The consecutive acetolysis, condensation with uracil and N6-benzoyladenine bis-trimethylsilyl derivatives and deblocking possessed phosphonate analogs of 5'-nucleotides in good yields. The intermediate 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose derivatives were used for the preparation of homonucleosides.

ChemInform Abstract: THE ARBUZOV REACTION OF TRIETHYL PHOSPHITE WITH ELEMENTAL IODINE

1980 ◽  
Vol 11 (17) ◽  
Author(s):  
A. SKOWRONSKA ◽  
M. PAKULSKI ◽  
J. MICHALSKI ◽  
D. COOPER ◽  
S. TRIPPETT
Keyword(s):  
Triethyl Phosphite ◽  
Arbuzov Reaction ◽  
The Arbuzov Reaction ◽  
Elemental Iodine

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.

scholarly journals Synthesis, kinetics and mechanism of nucleophilic substitution in octahedral (cat)2Sn(py)2

2005 ◽  
Vol 70 (12) ◽  
pp. 1389-1393 ◽  
Author(s):  
K.S. Siddiqi ◽  
Shahab Nami
Keyword(s):  
Nucleophilic Substitution ◽  
Rate Constant ◽  
Substitution Reaction ◽  
Molar Conductance ◽  
Chloride Ions ◽  
Kinetics And Mechanism ◽  
Nucleophilic Substitution Reaction ◽  
Nucleophilic Reagents

Dicatecholatodipyridinetin(IV) in nitrobenzene showed an increase in molar conductance with time, suggesting solvation of the complex. In the presence of nucleophilic reagents, such as SOCl2, C6H5COCl and CH3COCl, the conductance increased sharply owing to the substitution of pyridine by chloride ions. The data for the rate constant of solvation (k s) and for nucleophilic substitution (k 1 and k 2) have been calculated and it was found that the solvation is a slower process compared to the substitution by chloride ions, i.e., k1, k 2 > k s. The nucleophilic substitution reaction follows the SN1 mechanism.

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