A bis(heptafulvenyl)-dicyanoethylene thermoswitch with two sites for ring closure
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A bis(heptafulvenyl)-dicyanoethylene thermoswitch with two sites for ring closure. / Broman, Søren Lindbæk; Petersen, Anne Ugleholdt; Tortzen, Christian; Vibenholt, Johan Elias; Bond, Andrew; Nielsen, Mogens Brøndsted.
I: Organic Letters, Bind 14, Nr. 1, 2012, s. 318-321.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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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
Y1 - 2012
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
VL - 14
SP - 318
EP - 321
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 1
ER -
ID: 36047658