TY - JOUR
T1 - Synthesis and photochemistry of 3, 6-difluoro-10,11-benzopentacyclo-[6,4,0.02.7,03.12.06.9]dodeca-4,10-diene
AU - Kimura, Masaru
AU - Kura, Hisatoshi
AU - Nukada, Kastumi
AU - Okamoto, Hideki
AU - Satake, Kyosuke
AU - Morosawa, Shiro
PY - 1988/1/1
Y1 - 1988/1/1
N2 - 9,12-Difluoro-and 9,12-dichlorotetracyclo[6.4.2.29.12.02.7] hexadeca-2,4,6,13,15-pentaene-10,11 -dicarboxylic anhydrides (2a) and (2b) were prepared by 4πs + 4πs is photocycloaddition between cis-3,6-difluoro-or cis-3,6-dichloro-1,2-dihydrophthalic anhydride and naphthalene, respectively. 12, 15-Difluoro-and 12, 15-dichlorohexacyclo [8.6.0.02.15.03.8.09.12.011.16] hexadeca-3,5,7-triene-13,14-dicar-boxylic anhydrides (6a) and (6b) were obtained by 2πs + 2πs is intramolecular photocycloaddition of adducts (2a) and (2b), respectively. 12,15-Difluorohexacyclo[8.6.0.02.15.03.8.09.12.011.16]hexadeca-3,5,7,13-tetraene (7a) has been synthesized by the electro-oxidative decarboxylation of anhydride (6a) and the excited singlet naphthalene has been observed on irradiation of adduct (7a), and is presumably formed via an adiabatic pathway.
AB - 9,12-Difluoro-and 9,12-dichlorotetracyclo[6.4.2.29.12.02.7] hexadeca-2,4,6,13,15-pentaene-10,11 -dicarboxylic anhydrides (2a) and (2b) were prepared by 4πs + 4πs is photocycloaddition between cis-3,6-difluoro-or cis-3,6-dichloro-1,2-dihydrophthalic anhydride and naphthalene, respectively. 12, 15-Difluoro-and 12, 15-dichlorohexacyclo [8.6.0.02.15.03.8.09.12.011.16] hexadeca-3,5,7-triene-13,14-dicar-boxylic anhydrides (6a) and (6b) were obtained by 2πs + 2πs is intramolecular photocycloaddition of adducts (2a) and (2b), respectively. 12,15-Difluorohexacyclo[8.6.0.02.15.03.8.09.12.011.16]hexadeca-3,5,7,13-tetraene (7a) has been synthesized by the electro-oxidative decarboxylation of anhydride (6a) and the excited singlet naphthalene has been observed on irradiation of adduct (7a), and is presumably formed via an adiabatic pathway.
UR - http://www.scopus.com/inward/record.url?scp=37049074553&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=37049074553&partnerID=8YFLogxK
U2 - 10.1039/P19880003307
DO - 10.1039/P19880003307
M3 - Article
AN - SCOPUS:37049074553
SN - 1470-4358
SP - 3307
EP - 3310
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 12
ER -