Ring Expansions of Boroles with Diazo Compounds: Steric Control of C or N Insertion and Aromatic/Nonaromatic Products.
Access to novel imine-substituted 1,2-azaborinines, as well as highly arylated boracyclohexa-3,5-dienes has been developed by ring expansion of boroles with diazoalkanes with varying degrees of steric bulk. The formation of a diazoalkane intermediate is also discussed for the reaction of ortho-brominated p-tolyl-azide with 1,2,3,4,5-pentaphenylborole. Structural details as well as UV/Vis spectroscopic and cyclic voltammetric data are provided. These boron-containing heterocycles have the potential to serve as building blocks for boron-containing materials.
Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.ak-braunschweig.chemie.uni-wuerzburg.de/. h.braunschweig@uni-wuerzburg.de.
Holger
H
Braunschweig
Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.ak-braunschweig.chemie.uni-wuerzburg.de/
Florian
F
Hupp
Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.ak-braunschweig.chemie.uni-wuerzburg.de/
Ivo
I
Krummenacher
Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.ak-braunschweig.chemie.uni-wuerzburg.de/
Lisa
L
Mailänder
Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.ak-braunschweig.chemie.uni-wuerzburg.de/
Florian
F
Rauch
boron; diazo compounds; heterocycles; ring expansion; synthetic methods