Molecular Design of Tautomeric Compounds

Language: English

Published by Springer, Springer Netherlands Sep 2011, 2011

9401071403 / 9789401071406

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Neuware -Until the early seventies, tautomeric i. e. fast and reversible rearrangement reactions accompanied by migrations of carbon-centered groups - were practi cally unknown. For a long time it was assumed that the family of tautomeric reactions was confined to proto tropic transformations only. However, the discovery in the fifties of the reversible metallotropic rearrangements showed the domain of migratory tautomerism to be substantially broader. The synthesis of the metallotropic compounds was based on the substitution of a proton in prototropic compounds by an organometallic group. This approach rarely proved fruitful when attempting to effect tautomeric rearrangements of organic and organometallic groups formed by the elements to the right of carbon in the Periodic Table. By contrast, a novel approach involving an analysis of the steric requirements inherent in the structure of the transition state of a reactive center and an examination of the stereodynamic possibilities has given rise to a target-oriented molecular design of compounds capable of rapid and reversible intramolecular migration of the type indicated. The implementation of this ap proach, which is the subject of the present book, has already led to the preparation of new tautomeric compounds in which such heavy organic migrants as acyl, aryl, sulfinyl, phosphoryl, arsinyl, and other groups migrate in molecules at a frequency 6 9 of 10 -10 S-I at ambient temperature, i. e. , at the rates comparable with protonic migrations.

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Title
Molecular Design of Tautomeric Compounds
Author
V. I. Minkin
Publisher
Springer, Springer Netherlands Sep 2011
Publication year
2011
Condition
Neu
Binding
Taschenbuch
Language
English
ISBN 10
9401071403
ISBN 13
9789401071406
Item weight
515 grams
Dimensions
244x170x17 mm

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