Synthetic protocols for the key functionalizations of the photochromic dihydroazulene scaffold

TY - JOUR

T1 - Synthetic protocols for the key functionalizations of the photochromic dihydroazulene scaffold

AU - Cacciarini, Martina

AU - Broman, Søren Lindbæk

AU - Nielsen, Mogens Brøndsted

PY - 2014

Y1 - 2014

N2 - 1,8a-Dihydroazulene-1,1-dicarbonitrile (DHA) is a photochromic molecule which upon irradiation undergoes ring-opening to a vinylheptafulvene (VHF). The system has many possible sites for functionalization and hence for tuning of its properties. In this account we summarize different synthetic protocols for attaching substituents at the ring carbon atoms of DHA as well as for replacing the cyano groups at position 1. In particular, positions 2 and 7 are most easily accessed, the latter from DHA by a regioselective bromination-elimination protocol.

AB - 1,8a-Dihydroazulene-1,1-dicarbonitrile (DHA) is a photochromic molecule which upon irradiation undergoes ring-opening to a vinylheptafulvene (VHF). The system has many possible sites for functionalization and hence for tuning of its properties. In this account we summarize different synthetic protocols for attaching substituents at the ring carbon atoms of DHA as well as for replacing the cyano groups at position 1. In particular, positions 2 and 7 are most easily accessed, the latter from DHA by a regioselective bromination-elimination protocol.

U2 - 10.3998/ark.5550190.p008.475

DO - 10.3998/ark.5550190.p008.475

M3 - Journal article

SN - 1551-7004

VL - 2014

SP - 249

EP - 263

JO - A R K I V O C

JF - A R K I V O C

IS - 1

ER -