First synthesis of biquinoliziniun salts: novel example of a chiral azonia dication.
[Structure: see text] The 1,1'-, 2,2'-, and 3,3'-biquinolizinium dications are described for the first time and were prepared using palladium-catalyzed homocoupling reactions of the corresponding isomeric bromoquinolizinium bromides. Theoretical calculations show 1,1'- and 4,4'-biquinolizinium dications to be chiral molecules, the latter of which has a high energy of formation, a factor that probably precludes its formation.
García-Cuadrado
Domingo
D
Departamento de Química Orgánica and Departamento de Química Física, Universidad de Alcalá, Madrid, Spain.
Cuadro
Ana M
AM
Alvarez-Builla
Julio
J
Sancho
Unai
U
Castaño
Obis
O
Vaquero
Juan J
JJ
D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis*; D012492:Salts; D013237:Stereoisomerism
D011799:Quinazolines; D012492:Salts; D010165:Palladium