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Preparative Polar Organometallic Chemistry is a collection of laboratory procedures for the synthesis and functionalization of organoalkali and Grignard compounds. The second volume with methods for generation and transformation of compounds bearing the metal at an sp3 carbon complements the first in which the metal was bound to an sp2 carbon atom in the reagent. Synthetically important intermediates such as metallated S, S-acetales, imines, nitriles, isonitriles and ketones are illustrated. All procedures have been worked out in full detail and tested in the author's own laboratory. Both books are intended to be practical bench-top laboratory manuals for working organic chemists, from the student to the advanced scientist.
Polar organometallic compounds are indispensable for the synthetic chemist. As this book shows, these almost ideal reagents are easy to prepare with high specificity under mild conditions and yet react quite readily with a great variety of substrates. Many compounds can be metallated directly at positions which would otherwise be difficult to substitute. Functional groups and heteroatoms already present in a molecule direct metallation to sites in their vicinity. The rules which govern polar organometallic chemistry often are not dominated by the usual n-delocalization and inductive effects; dipolar interactions, chelation, polarization, etc. often can be much more important. This affords novel synthetic opportunities. A good example is the development of a basically new type of aromatic substitution chemistry not based on positively charged intermediates. Seebach's injunction, "Thinking of polar organometallic compounds as carbanions is an impoverishment rather than a simplification" (International Symposium, Chemistry of Carbanions, Durham 1984), stresses the need to consider the metal not only as an integral, but perhaps also as the key component of these reagents. Rather than wandering off as solvated cations and acting as uninvolved spectators, the metals, rather than the anion moieties, can initiate and govern the subsequent reactions. To the founders of this field, e. g. Grignard, Ziegler, Gilman, Wittig, and their followers, the metal was critical. The title of Schlosser's book, "Polare Organometalle," certainly was apt.
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