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Synthesis of Azulenes

The azulenes constitute the best known class of polycyclic nonbenzenoid aromatic compounds and have long fascinated chemists with their remarkable colors and unusual electronic properties. We have developed several versatile methods for the regiocontrolled synthesis of substituted azulenes.

References:

"A New Synthesis of Substituted Azulenes", D. A. Becker and R. L. Danheiser, J. Am. Chem. Soc. 1989, 111, 389.

"A Ring Expansion-Annulation Strategy for the Synthesis of Substituted Azulenes. Preparation and Suzuki Coupling Reactions of 1-Azulenyl Triflates", J. L. Kane, K. M. Shea, A. L. Crombie, and R. L. Danheiser, Org. Lett. 2001, 3, 1081.

[ Home ] [ [2 + 2 + 2] Cycloaddition Strategies ] [ [3 + 2] Annulations of Organosilanes ] [ Vinylcyclopropane Rearrangements ] [ Cycloadditions and Annulations of Vinylketenes ] [ Highly Unsaturated, Conjugated Molecules ] [ [4 + 2] Cycloadditions of Imine Derivatives ] [ Ketene [2 + 2] Cycloadditions ] [ Acylsilanes ] [ B-Lactones ] [ Cyclopropylboranes ] [ Allenylsilanes and Homopropargylic Alcohols ] [ Cationic Cyclizations ] [ Synthesis of Azulenes ] [ Miscellaneous Synthetic Methods ]