Diels-Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines. Synthesis and X-ray crystal structures of diazafluoranthene derivatives.
The synthesis of a series of 3,6-disubstituted-1,2,4,5-tetrazines has been effected using an inverse electron demand [2 + 4] cycloaddition strategy. The crystal structures of 18 members of this series of diazafluoranthenes are reported. Stereochemical analysis shows that diazafluoranthenes, substituted across the bay region, are helically-twisted strained aromatic molecules. The dihedral angle between pyridazyl vs naphthyl rings ranges from 0.5 degrees to 20.9 degrees, and follows the degree of steric congestion in the bay region. The crystal structures are compared to computational structures determined using density functional theory, with the M06-2X/cc-pVDZ method.
Organish-Chemisches Institute, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland.
Nelli
N
Rahanyan
Anthony
A
Linden
Kim K
KK
Baldridge
Jay S
JS
Siegel