TY - JOUR
T1 - On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch
AU - Mazzanti, Virginia
AU - Cacciarini, Martina
AU - Broman, Søren Lindbæk
AU - Parker, Christian Richard
AU - Schau-Magnussen, Magnus
AU - Bond, Andrew
AU - Nielsen, Mogens Brøndsted
PY - 2012/6/27
Y1 - 2012/6/27
N2 - Background: The dihydroazulene (DHA)/vinylheptafulvene (VHF) system (with two cyano groups at C1) functions as a photo-/thermoswitch. Direct ionic bromination of DHA has previously furnished a regioselective route to a 7,8-dibromide, which by elimination was converted to a 7-bromo-substituted DHA. This compound has served as a central building block for functionalization of the DHA by palladium-catalyzed cross-coupling reactions. The current work explores another bromination protocol for achieving the isomeric 3-bromo-DHA and also explores the outcome of additional bromination of this compound as well as of the known 7-bromo-DHA.
AB - Background: The dihydroazulene (DHA)/vinylheptafulvene (VHF) system (with two cyano groups at C1) functions as a photo-/thermoswitch. Direct ionic bromination of DHA has previously furnished a regioselective route to a 7,8-dibromide, which by elimination was converted to a 7-bromo-substituted DHA. This compound has served as a central building block for functionalization of the DHA by palladium-catalyzed cross-coupling reactions. The current work explores another bromination protocol for achieving the isomeric 3-bromo-DHA and also explores the outcome of additional bromination of this compound as well as of the known 7-bromo-DHA.
U2 - 10.3762/bjoc.8.108
DO - 10.3762/bjoc.8.108
M3 - Journal article
C2 - 23015846
SN - 2195-951X
VL - 8
SP - 958
EP - 966
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
ER -