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Approach to the Blues: A Highly Flexible Route to the Azulenes
Author(s) -
Carret Sébastien,
Blanc Aurélien,
Coquerel Yoann,
Berthod Mikaël,
Greene Andrew E.,
Deprés JeanPierre
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200501276
Subject(s) - blues , ring (chemistry) , chemistry , cycloaddition , dimethylformamide , palette (painting) , organic chemistry , computer science , art , solvent , catalysis , art history , operating system
A palette of blues : Chlorobicyclo[5.3.0]decatrienones are readily prepared from cycloheptatrienes by cycloaddition of dichloroketene, ring expansion with a diazoalkane, and dehydrochlorination in dimethylformamide. These compounds are used as intermediates in the regiocontrolled synthesis of a wide variety of natural and nonnatural azulenes (see scheme).