6Pi e- versus 8pi e- electrocyclization of 1-aryl- and heteroaryl-substituted (1Z,3Z)-1,3,5-hexatrienes: a matter of aromaticity.
Peri selectivity of the electrocyclization of 1-aryl- and heteroaryl-substituted (1Z,3Z)-1,3,5-hexatrienes, obtained by Ru-catalyzed linear coupling of 1,6-diynes to Z-propenyl(hetero)arenes, can be efficiently modulated depending on the aromaticity of the (hetero)arene: 1,3,5-hexatrienyl(hetero)arenes give 8pi e- electrocyclization with the exception of 1,3,5-hexatrienylbenzenes, which give 6pi e- electrocyclization.
García-Rubín
Silvia
S
Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Varela
Jesús A
JA
Castedo
Luis
L
Saá
Carlos
C