Reformatskii reaction

The Reformatskii reaction was carried with the dimethyl xanthate ester (58) ... 

Gaudemar, M. Reformatskii reaction during the last thirty years. Organometallic Chemistry Reviews, Section A Subject Reviews 1972, 8, 183-233. 

Fuerstner, A. Recent advancements in the Reformatskii reaction. Synthesis 1989, 571-590. 

Marshall, J. A. Rhodium-catalyzed Reformatskii reaction. Chemtracts 2000,13, 705-707. 

Moriwake, T. Reformatskii reaction. I. Condensation of ketones and tert-butyl bromoacetate by magnesium. J. Org. Chem. 1966, 31, 983-985. 

Mainz, J., Arrieta, A., Lopez, X., Ugalde, J. M., Cossio, F. P., Lecea, B. Transition structures for the Reformatskii reaction. Atheoretical (MNDO-PM3) study. Tetrahedron Lett. 1993, 34, 6111-6114. 

Loeffler, A., Pratt, R. D., Pucknat, J., Gelbart, G., Dreiding, A. S. Preparation of a-methylenebutyrolactones by the Reformatskii reaction synthesis of protolichesterinic acid. Chimia 1969, 23, 413-416. 

Stamm, H., Steudie, H. Nitrones. Xi. isoxazoiidine compounds. Viii. N-substituted 5-isoxazoiidinones by Reformatskii reaction with nitrones. Tetrahedron 1979, 35, 647-650. 

Gabriel, T., Wessjohann, L. The chromium-Reformatskii reaction asymmetric synthesis of the aldol fragment of the cytotoxic epothilons from 3-(2-bromoacyl)-2-oxazolidinones. Tetrahedron Lett. 1997, 38, 1363-1366. 

Reformatskii reaction. Condensation of carbonyl compounds with organozinc derivatives of a-halo esters to yield (i-hydroxy esters. 

N. S. Vul fson and L. Kh. Vinograd, in Reactions and Research Methods for Organic Compounds, Book 17 Reformatskii Reaction , Khimiya, Moscow, 1967. 

In terms of the yield and reaction rate, the Reformatskii reaction is a rather convenient route to biologically active 3-methylene-substituted 2-oxo-l,2-oxaphosphacyclanes 85, including those having a spiro-structure (Scheme 52) [116, 117]. Metal-catalysed formation of the P-C bond was also successfully used for the synthesis of similar phostones [118]. Thus, 3-methylene-1,2-oxaphosphacycla-nes 85 were formed in reasonable yields by palladium-catalysed intramolecular cyclization in a series of hydrophosphoryl compounds 86 (Scheme 52). 

The Reformatskii reaction of C-methyl-A -phenylnitrone, MeCH=N(Ph)—O", with ethyl bromoacetate furnishes the isoxazolidinone... 

Taguchi, T. Kitagawa, O. Suda, Y. Ohkawa, S. Hashimoto, A. litaka, Y. Kobayashi, Y. Synthesis of 3,3-difluoro-2-azetidinones and 2,3-dideoxy-2,2-difluoro-3-aminosugars through the Reformatskii reaction of difluoroacetate with imine. Tetrahedron Lett. 1988, 29(41), 5291-5294. 

Additive in Various Reduction Systems. TMSCl has been employed in many different reduction systems to improve the reactivity and/or increase the selectivity. The reagent has been used to activate zinc dust or as additive for Reformatskii reactions. While less reactive than Mg/TMSCl combination, the Zn/TMSCl combination proved to be the preferred reagent system for large scale and high concentrated preparation of diamines through the pinacol coupling of two molecules of imines (eq 76). ... 

Reformatsky (Reformatskii) Reaction Reimer-Tiemann Reaction... 

The Reformatskii reaction can be carried out conveniently with magnesium. If tert-huiy esters are used, the products can subsequently be transformed into satd. acids in a single operation Another easy method for the conversion of aldehydes to nitriles is their treatment with lead tetraacetate and ammonia in benzene Hydrocyanations can be efficiently performed with the help of organoaluminum compounds In this manner, steroidal cyanohydrins can be obtained from the respective epoxides by diaxial fission under mild conditions in high yield A number of addition reactions of nitrile oxides have been reported contrary to earlier reports, ar. nitrile oxides easily add hydrogen halides. 

Schwarz KH, Kleiner K, Ludwig R, Schick H (1992) Electrochemically supported Reformatskii reaction a convenient preparation of 2-substituted 1-ethyl 3-oxoaIkanedioates. J Org Chem 57 4013 015. doi 10.1021/jo00040a051... 

Carbon-14 labels can be introduced into the retinoic acid molecule by an appropriately labeled senecioic acid ester. When the method incorporated the use of [ CJcarboxyl senecioic acid, which is easily prepared from isocrotylmag-nesium bromide and " C02, it was preferable to the method using the Reformatskii reaction [compare Section II,A,l,a,i] for the preparation of carboxyl-labeled all-rranj-retinoic acid (Wursch, 1960). 

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