A bis(heptafulvenyl)-dicyanoethylene thermoswitch with two sites for ring closure

TY - JOUR

T1 - A bis(heptafulvenyl)-dicyanoethylene thermoswitch with two sites for ring closure

AU - Broman, Søren Lindbæk

AU - Petersen, Anne Ugleholdt

AU - Tortzen, Christian

AU - Vibenholt, Johan Elias

AU - Bond, Andrew

AU - Nielsen, Mogens Brøndsted

N1 - © 2011 American Chemical Society

PY - 2012/1/6

Y1 - 2012/1/6

N2 - Suitably functionalized vinylheptafulvenes (VHFs) act as thermoswitches undergoing ring closure to the corresponding dihydroazulenes (DHAs). Here we present the synthesis of a new such thermoswitch incorporating two heptafulvene rings on a dicyanoethylene unit. The synthetic protocol explores both the tropylium species as an electrophile and as a leaving group in the generation of the heptafulvene units. The thermally induced ring closure was enhanced as a result of two accessible sites for the reaction to occur.

AB - Suitably functionalized vinylheptafulvenes (VHFs) act as thermoswitches undergoing ring closure to the corresponding dihydroazulenes (DHAs). Here we present the synthesis of a new such thermoswitch incorporating two heptafulvene rings on a dicyanoethylene unit. The synthetic protocol explores both the tropylium species as an electrophile and as a leaving group in the generation of the heptafulvene units. The thermally induced ring closure was enhanced as a result of two accessible sites for the reaction to occur.

KW - Cyanates

KW - Ethylenes

KW - Models, Molecular

KW - Molecular Structure

U2 - 10.1021/ol2030586

DO - 10.1021/ol2030586

M3 - Journal article

C2 - 22148908

SN - 1523-7060

VL - 14

SP - 318

EP - 321

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -