Arbuzov phosphonate synthesis

Phosphonate synthesis from the reaction of alkyl halides 

Kiddle, J. J. Gurley, A. F. Phosphorus, Sulfur Silicon Relat. Elem. 2000,160,195. Bhattacharya, A. K. Stolz, F. Schmidt, R. R. Tetrahedron Lett. 2001,42, 5393. Nifantiev, E. E. Khrebtova, S. B. Kulikova, Y. V. Predvoditelev, D. A. Kukhareva, T. S. Petrovskii, P. V. Rose, M. Meier, C. Phosphorus, Sulfur Silicon Relat. Elem. 2002,177,251. 

Asymmetric reduction of ketones using Alpine-borane . Alpine-borane = fi-isopinocampheyl-9-borabicyclo[3.3.1]nonane. 

Tejima, M. Ebiike, H. Achiwa, K. Chem. Pharm. Bull. 1996, 44, 1132. Waschbiisch, R. Carran, J. Marinetti, A. Savignac, P. Synthesis 1997,121. 

Phosphonate synthesis from the reaction of alkyl halides with phosphites. General scheme  

Ordonez, M. Hemandez-Femandez, E. Montiel-Perez, M. Bautista, R. Bustos, P. Rojas-Cabrera, H. Femandez-Zertuche, M. Garcia-Barradas, O. Tetrahedron Asymmetry 2007,18, 2427-2436. 

Name Reactions, 4fb ed., DOI 10.1007/978-3-642-01053-8 162, Springer-Verlag Berlin Heidelberg 2009 

Midland reduction. In Name Reactions for Functional Group Transformations, Li, J. J., Corey, E. J., Eds. Wiley Sons Hoboken, NJ, 2007, pp 40-45. (Review). 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 174, Springer International Publishing Switzerland 2014 

Agnaniet, H. Leydet, A. Montero, J.-L. Phosphorus, Sulfur Silicon Relat. Elem. 1997, 129, 83. 

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MICHAELIS-ARBUZOV Phosphonate Synthesis Ni catalyzed phosphonate synthesis from phosphites and aryl halides. Reaction of alkyl halides with phosphites proceeds without nickel salts (see 1st edition). 

ALPER Carbonylalion 2 AMADORI Glucosamine rearrangement 3 ANGELl - RIMINI Hydroxarrw acid synthesis 4 ARBUZOV - MICHAELIS Phosphonate synthesis 5... 

The phosphonates obtained by the Arbuzov reaction are starting materials for the Wittig-Homer reaction (Wittig reaction), for example, appropriate phosphonates have been used for the synthesis of vitamin A and its derivatives/... 

Example 57 the synthesis of 2-chloro-iV -methyladenine-9-(2-methyl-propyl)bis phosphonate, analogous to the corresponding bisphosphate, has been performed by Jacobson and associates [93]. The key step in this synthesis is the Arbuzov-Michaelis reaction. 

Sugars containing a carbon-phosphorus bond have been prepared by application of the Michaelis-Arbuzov reaction to bromodeoxy sugars. Thus, the reaction of 5-bromo-5-deoxy-l,2-0-isopropylidene-3-O-methyl-a-D-xylofuranose (131) with triethyl phosphite yields the corresponding diethyl phosphonate (132) compound 132 was employed for the synthesis of a sugar derivative having phosphorus as... 

Diethyl [(2-tetrahydropyranyloxy)methyl]phosphonate is useful in the Wlttig-Horner synthesis of enol ethers, which are intermediates in one-carbon homologations of carbonyl compounds. This procedure is an adaptation of a general method for making dialkyl hydroxymethylphosphonates. An 0-tetra-hydropyranyl derivative also has been made from dibutyl hydroxymethyl -phosphonate, and diethyl hydroxymethylphosphonate has been O-silylated with tert-butylchiorodimethylsilane and imidazole. Another useful congener in this series has been prepared by an Arbuzov reaction of methoxyethoxymethyl (HEM) chloride and triethyl phosphite. 

Briefly we review the chemical improvements which we achieved in the oxoalkylphosphonates field which represent the key compounds. Phosphonic aldehydes are obtained in adapting the Arbuzov procedure to 6 or V haloketals (4). A modification of the phospho-nylation conditions (t°, stoichiometry) followed by removal of the protecting group in dilute acid and then continuous extraction allows synthesis of suitably branched compounds on a large scale (5). 

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