2,4,6-Triphenylpyrylium tetrafluoroborate-photosensitized reactions of o-cinnamylphenols and o-hydroxystilbenes

被引：7

作者：

Delgado, J ^{[1
]}

Espinos, A ^{[1
]}

Jimenez, MC ^{[1
]}

Miranda, MA ^{[1
]}

Tormos, R ^{[1
]}

机构：

[1] UNIV POLITECN VALENCIA,CSIC,INST TECNOL QUIM,DEPT QUIM,E-46071 VALENCIA,SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(96)01010-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct irradiation of o-cinnamylphenols 1a-c led to mixtures of the cis-isomers 3a-c, the dihydrobenzofurans 4a-c and the dihydrobenzopyrans 5a-c. Under the same conditions, o-hydroxystilbenes 2a,b gave their cis-isomers 9a,b as single photoproducts. Using 2,4,6-triphenylpyrylium tetrafluoroborate as photosensitizer the reactions of the methyl- or methoxy- substituted derivatives appear to proceed via single electron transfer. Compounds 1b,c underwent oxidative fragmentation to the aldehydes 8b,c, while 2b cyclized to benzofuran 10b. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：681 / 688

页数：8

共 17 条

[1] BAUER DJ, 1983, ANTIVIR RES, P235
[2] SYNTHESIS AND CALCIUM ANTAGONISTIC ACTIVITY OF A SERIES OF DIETHYL BENZOFURYL, BENZOTHIENYL AND BENZOGAMMAPYRONYL BENZYLPHOSPHONATES
BAZIARDMOUYSSET, G
TCHANI, GW
STIGLIANI, JL
PAYARD, M
BONNAFOUS, R
TISNEVERSAILLES, J
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (7-8) : 539 - 546
[3] POLYMERISATION OF FLAVANS .6. REDUCTION OF FLAVANOIDS AND CHALCONES WITH LITHIUM ALUMINIUM HYDRIDE IN PRESENCE OF ALUMINIUM CHLORIDE
BOKADIA, MM
BROWN, BR
ROBERTS, A
SOMERFIELD, GA
COBERN, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAY): : 1658 - &
[4] PHOTOINDUCED ELECTRON-TRANSFER WITHIN ZEOLITE CAVITIES - CIS-STILBENE ISOMERIZATION PHOTOSENSITIZED BY 2,4,6-TRIPHENYLPYRYLIUM CATION IMPRISONED INSIDE ZEOLITE-Y
CORMA, A
FORNES, V
GARCIA, H
MIRANDA, MA
PRIMO, J
SABATER, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2276 - 2280
[5] FOX MA, 1988, PHOTOINDUCED ELEC AD
[6] INVOLVEMENT OF OXIRANE INTERMEDIATES IN THE ELECTRON-TRANSFER PHOTOOXYGENATION OF 1,1-DIARYLETHYLENES AND 1,2-DIARYLETHYLENES SENSITIZED BY 2,4,6-TRIPHENYLPYRYLIUM TETRAFLUOROBORATE
GARCIA, H
MIRANDA, MA
MOJARRAD, F
SABATER, MJ
[J]. TETRAHEDRON, 1994, 50 (29) : 8773 - 8780
[7] Gilbert A., 1991, ESSENTIALS MOL PHOTO
[8] PHOTOCHEMISTRY OF ALLYLPHENOL DERIVATIVES - ROLE OF THE PHENOLIC AND STYRENIC EXCITED-STATES IN THE BEHAVIOR OF BICHROMOPHORIC CINNAMYLPHENOL
JIMENEZ, MC
MARQUEZ, F
MIRANDA, MA
TORMOS, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) : 197 - 202
[9] OXIDATION OF FLAVANONES USING THALLIUM(III) SALTS - A NEW ROUTE FOR THE SYNTHESIS OF FLAVONES AND ISOFLAVONES
KHANNA, MS
SINGH, OV
GARG, CP
KAPOOR, RP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (19): : 2565 - 2568
[10] M'Sadek M., 1992, B SOC CHIM BELG, V101, P323

← 1 2 →