Organic synthesis, reactive

MacGillivray, L. R. Reid, J. L. Ripmeester, J. A. Papaefstathiou, G. S. Toward a Reactant Library in Template-Directed Solid-State Organic Synthesis Reactivity Involving a Mono-Functional Reactant Based on a Stilbazole. Indust. Eng. Chem. Res. 2002, 41, 4494. 

R. C. Larock, Organomercury Compounds in Organic Synthesis (Reactivity and Structure Concepts in Organic Chemistry), Vol. 22. Springer-Verlag, Berlin, 1985. 

Weber, W.P. Gokel G.W. Phase Transfer Catalysis in Organic Synthesis Reactivity and Structure in Organic Chemistry 4 ... 

Kurihara, T., Santo, K., Harusawa, S., and Yoneda, R., Application of cyanophosphates in organic synthesis. Reactivity of a-cyano-a-diethylphosphonooxy anions, Chem. Pharm. Bull.. 35, 4777, 1987. 

Library of Congress Cataloging in Publication Data. Weber, William P 1940-. Phase transfer catalysis in organic synthesis. (Reactivity and structure v. 4) Includes bibliographies and indexes. 1. Catalysis. 2. Chemistry, Organic—Synthesis. I. Gokel, G. W., 1946- joint author. II. Title. III. Series. QD505.W4. 547.2. 77-22798... 

A few years after the first articles of Breslow had appeared, Grieco elegantly demonstrated that the astonishing rate and selectivity enhancements of Diels-Alder reactions in water can be exploited sirccessfully in organic synthesis. He extensively studied the reactivity of dienes containing... 

Dichloroacetic acid [79-43-6] (CI2CHCOOH), mol wt 128.94, C2H2CI2O2, is a reactive intermediate in organic synthesis. Physical properties are mp 13.9°C, bp 194°C, density 1.5634 g/mL, and refractive index 1.4658, both at 20°C. The Hquid is totally miscible in water, ethyl alcohol, and ether. Dichloroacetic acid K = 5.14 X 10 ) is a stronger acid than chloroacetic acid. Most chemical reactions are similar to those of chloroacetic acid, although both chlorine... 

Ethers are among the most used protective groups in organic synthesis. They vary from the simplest, most robust, methyl ether to the more elaborate, substituted, trityl ethers developed for use in nucleotide synthesis. They are formed and removed under a wide variety of conditions. Some of the ethers that have been used to protect alcohols are included in Reactivity Chart 1. ... 

W. P. WF-BERandC. W. GOKEL, Phase Transfer Catalysis in Organic Synthesis, Vol. 4 of Reactivity and Structure, Springer-Verlag, 1977, 250 pp. C. M. Starks and C. Uotta, Phase Transfer Catalysis, Academic Press, New York, 1978, 365 pp. F. MontanaRI, D. Landini and F. Rolla, Topics in Current Chemistry 101, 149-201 (1982). E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis (2nd edn.), VCH Publishers. London 1983, 386 pp. T. G. Southern, Polyhedron 8. 407-13 (1989). 

Because of their manifold reactivity, Mannich bases 4 are useful intermediates in organic synthesis. For example the elimination of amine leads to formation of an o ,/3-unsaturated carbonyl compound 8 ... 

The overall process is the addition of a CH-acidic compound to the carbon-carbon double bond of an o ,/3-unsaturated carbonyl compound. The Michael reaction is of particular importance in organic synthesis for the construction of the carbon skeleton. The above CH-acidic compounds usually do not add to ordinary carbon-carbon double bonds. Another and even more versatile method for carbon-carbon bond formation that employs enolates as reactive species is the aldol reaction. 

Reetz, M. T. Organotitanium Reagents in Organic Synthesis. A Simple Means to Adjust Reactivity and Selectivity of Carbanions. 106, 1-53 (1982). 

Intermediates 18 and 19 are comparable in complexity and complementary in reactivity. Treatment of a solution of phosphonium iodide 19 in DMSO at 25 °C with several equivalents of sodium hydride produces a deep red phosphorous ylide which couples smoothly with aldehyde 18 to give cis alkene 17 accompanied by 20 % of the undesired trans olefin (see Scheme 6a). This reaction is an example of the familiar Wittig reaction,17 a most powerful carbon-carbon bond forming process in organic synthesis. 

In the fifty or so years since the discovery of a-metalated epoxides, our understanding of their reactivity has advanced to such a level that their use in routine organic synthesis is now possible. Many research groups continue to examine their unusual reaction pathways and to develop these into synthetically useful processes. In contrast, the chemistry of a-metalated aziridines is still in its infancy and there are undoubtedly many interesting facets of their nature still to be explored and applied in organic synthesis. 

In 20 years of usage, a,/J-unsaturated Fischer carbene complexes demonstrated their multitalented versatility in organic synthesis, yet new reaction types are still being discovered every year. In view of their facile preparation and multifold reactivity, their versatile chemistry will undoubtedly be further developed and applied in years to come. The application of chirally modified Fischer carbene complexes in asymmetric synthesis has only begun, and it will probably be an important area of research in the near future. 

Dihydro-1-vinylnaphthalene (67) as well as 3,4-dihydro-2-vinylnaphtha-lene (68) are more reactive than the corresponding aromatic dienes. Therefore they may also undergo cycloaddition reactions with low reactive dienophiles, thus showing a wider range of applications in organic synthesis. The cycloadditions of dienes 67 and 68 and of the 6-methoxy-2,4-dihydro-1-vinylnaphthalene 69 have been used extensively in the synthesis of steroids, heterocyclic compounds and polycyclic aromatic compounds. Some of the reactions of dienes 67-69 are summarized in Schemes 2.24, 2.25 and 2.26. In order to synthesize indeno[c]phenanthrenones, the cycloaddition of diene 67 with 3-bromoindan-l-one, which is a precursor of inden-l-one, was studied. Bromoindanone was prepared by treating commercially available indanone with NBS [64]. 

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