TY - JOUR
T1 - Synthesis of new sulfur heteroaromatics isoelectronic with dibenzo[g,p]chrysene by photocyclization of thienyl- and phenyl-substituted ethenes
AU - Fischer, Erik
AU - Larsen, Jan
AU - Christensen, Jørn B.
AU - Fourmigué, Marc
AU - Madsen, Hans G.
AU - Harrit, Niels
PY - 1996/10/4
Y1 - 1996/10/4
N2 - A series of new sulfur heteroarenes, isoelectronic with dibenzo[g,p]chrysene, have been prepared by double photocyclization of the corresponding tetraaryl substituted ethenes. The first step proceeds efficiently in each case, and the corresponding intermediate sulfur heteroarenes, isoelectronic with phenanthrene, have been isolated. The second ring closure is only efficient when one of the participating aryl substituents is thienyl, which thus manifests a higher electron density on the carbon atom involved in the excited singlet state reaction. Most of the new compounds are of minimal solubility in common solvents and do not display improved electron donor properties otherwise commonly found among heteroaromatics.
AB - A series of new sulfur heteroarenes, isoelectronic with dibenzo[g,p]chrysene, have been prepared by double photocyclization of the corresponding tetraaryl substituted ethenes. The first step proceeds efficiently in each case, and the corresponding intermediate sulfur heteroarenes, isoelectronic with phenanthrene, have been isolated. The second ring closure is only efficient when one of the participating aryl substituents is thienyl, which thus manifests a higher electron density on the carbon atom involved in the excited singlet state reaction. Most of the new compounds are of minimal solubility in common solvents and do not display improved electron donor properties otherwise commonly found among heteroaromatics.
UR - http://www.scopus.com/inward/record.url?scp=0000408854&partnerID=8YFLogxK
U2 - 10.1021/jo960022x
DO - 10.1021/jo960022x
M3 - Journal article
AN - SCOPUS:0000408854
VL - 61
SP - 6997
EP - 7005
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -