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: Henning Hopf, Michael S. Sherburn
: Cross Conjugation: Modern Dendralene, Radialene and Fulvene Chemistry
: Wiley-VCH
: 2016
ISBN: 978-3527334377
: English
: pdf
: 24,4 mb
: 480

Cross-conjugation has been important since the dawn of organic chemistry. The first compound synthesized, urea, contains a cross-conjugated ?-system. Cross-conjugated structures also played a vital role in the early development of industrial organic chemistry in the mid nineteenth century. Synthetic tri-arylmethane compounds, and specifically the cationic dyes derived therefrom, contain cross-conjugated ?-systems. The natural dyestuff indigo, first produced by extraction and later by industrial synthesis, also contains a cross-conjugated ?-system.

Thematically, this book is organized along very simple structural principles. You start with a review of the (carbo-)dendralenes, a class of compounds lying dormant for many years, but receiving growing attention recently. Then you move on to the heterodendralenes, which result by replacing one or more of the sp2-hybridized carbon atoms of the parent hydrocarbons by heteroatoms, most often oxygen, sulfur, or nitrogen. Next move to the (carbo-)radialenes and heteroradialenes, formally derived from the dendralenes by replacing the two penultimate (methine) protons of their terminal double bonds by an intramolecular C-C o-bond.

A final section covers the use of cross-conjugated compounds in synthesis. Besides the preparation of metal complexes of these compounds, particular emphasis lies on the use of carbodendralenes for the rapid generation of molecular complexity and - as one typical example for the practical application of heterodendralenes - in Nazarov cyclizations.

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