Condensation Ivanov

Zimmerman-Traxler Transition State Ivanov condensation JACS 1957, 7.9, 1920. 

From a historical standpoint, the Zimmerman-Traxler study on the stereochemical aspects of the Ivanov reaction is of considerable significance (22). Their investigation revealed that the magnesium enediolate 19a, upon condensation with benzaldehyde (Et2 O, reflux 5 hr), afforded the erythro and threo acids 20E and 20T, respectively, in a 24 76 ratio (eq. [13]). In the analysis of plausible transition states, both chair A and boat B geometries were considered. Zimmerman and Traxler concluded that the major diastereomer 20T could... 

The acidity of thermal waters usually ranges within pH =1-3, but more acid waters are often encountered (pH less than one and even sometimes less than zero) (Ivanov, 1956). The mineralization of such waters varies with the variation in acidity. In thermal waters which are the condensate of the high-temperature stage with pH less than one, the mineralization is more than 12 g/1. However, from recent manifestations in the Kamchatka volcanic arc only a few cases can be cited where the ionic force of the waters exceeded 0.5. Only the pore solutions are highly mineralized the freely circulating waters have low ionic force (Sidorov, 1967). As lava cools the acidity of the waters decreases and thus so does their mineralization whereas at pH = 2 the mineralization amounts to 0.6-1.2 g/1 (chloride-sulfate composition), at pH = 5-6 the mineralization amounts to 0.2-0.3 g/1 (slightly acid waters, increased role of COj) (Basharina, 1963). 

Ivanov reagent. Reaction product of aryl acetic acids and excess Grignard reagent. The reagent may be used in condensations with carbonyl compounds and other Grignard-type reactions. 

Agranovich, V. M. (2007). Hybrid organic-inorganic nanostructures and light-matter interaction. In Problems of Condensed Matter, edited by A. L. Ivanov and S. G. Tikhodeev. Clarendon Press, Oxford, pp. 24-43. 

A. L. Ivanov, S. G. Tikhodeev Problems of condensed matter physics—quantum coherence phenomena in electron—hole and coupled matter-light systems 138. I. M. Vardavas, F. W. Taylor Radiation and climate 137. A. F. Borghesani Ions and electrons in liquid helium 136. C. Kiefer Quantum gravity, Second edition... 

The interaction between the sodium salt of phenylacetic acid and isopropyl magnesium bromide results into a doubly charged species known as the Ivanov reagent. This product on treatment with cyclopentanone affords aldol condensation to yield the corresponding hydroxy acid. The resulting product on being subjected to alkylation with N-(2-chloro-ethyl)-dimethylamine gives the desired official compound. 

Besides the aldol reaction to form y0-hydroxyketone, 1,3-Dipolar Cycloaddition can also form similar molecules. In addition to the Mukaiyama Aldol Reaction, the following are also similar or closely related to the aldol reaction the Claisen-Schmidt Condensation (the aldol reaction between benzaldehyde and an aliphatic aldehyde or ketone in the presence of relatively strong bases to form an o, )0-unsaturated aldehyde or ketone), the Henry Reaction (base-catalyzed addition of nitroalkane to aldehydes or ketones), the Ivanov Reaction (the addition of enediolates or aryl acetic acid to electrophiles, especially carbonyl compounds), the Knoevenagel Reaction (the condensation of aldehydes or ketones with acidic methylene compounds in the presence of amine or ammonia), the Reformatsky Reaction (the condensation of aldehydes or ketones with organozinc derivatives of of-halo-esters), and the Robinson Annulation Reaction (the condensation of ketone cyclohexanone with methyl vinyl ketone or its equivalent to form bicyclic compounds). 

Historical perspective C. H. Heathcock, Comp. Org. Syn. 2, 133-179 (1991). General review T. Mukaiyama, Org. React. 28,203-331 (1982). Application of lithium and magnesium enolates C. H. Heathcock, Comp. Org. Syn. 2, 181-238 (1991) of boron enolates B. M. Kim etal, ibid. 239-275 of transition metal enolates I. Paterson, ibid. 301-319. Stereoselective reactions of ester and thioester enolates M. Braun, H. Sacha, J. Prakt. Chem. 335,653-668 (1993). Review of asymmetric methodology A. S. Franklin, I. Paterson, Contemp. Org. Syn. 1,317-338 (1994). Cf. Claisen-Schmidt Condensation Henry Reaction Ivanov Reaction Knoevenagel Condensation Reformatskv Reaction Robinson Annulation. 

Early reviews B. Blagoev, D. Ivanov, Synthesis 1970, 615 D. Ivanov etal., ibid. 1975, 83. Synthetic application Y. A. Zhdanov etal, Carbohyd. Res. 29,274 (1973). Kinetic and mechanistic study J. Toullec etal, J. Org. Chem. 50,2563 (1985). Stereoselectivity M. Mladenova etal. Tetrahedron 37,2157 (1981) M. Momtchev etal. Bull Soc. Chim. France 5, 844 (1985). Cf. Aldol Reaction Knoevenagel Condensation. 

Berlin, A. A., Mel nikov, V G., and Ivanov, N. S., Catalytic effect and inhibitory activity of some polysulfophenylenequinones on the condensation telomerization reaction, Plast. Massi, 1966, No. 1, p. 34 (Russian). 

Ivanov, A.V., LA. Ushakov, K.B. Petrushenko et al. 2010. Chemo-, regio- and stereospecific synthesis of novel unnatural fluorescent amino acids via condensation of L-lysine and l-vinylpyrrole-2-carbaldehydes. EurJ Org Chem 24 4554-4558. 

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