Photochemistry of bicyclo[2.2.2]octenones: an uncommon oxidative decarbonylation

被引:20
作者
Lee, TH [1 ]
Rao, PD [1 ]
Liao, CC [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
关键词
D O I
10.1039/a901182j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several substituted 3,3-dialkoxy-5-methoxycarbonyIbicyclo[2.2.2]oct-5-en-2-ones underwent unusual oxidative decarbonylation to produce polysubstituted cyclohexenes upon direct irradiation and usual ODPM rearrangement under sensitized conditions. A plausible mechanism for the oxidative decarbonylation is also given.
引用
收藏
页码:801 / 802
页数:2
相关论文
共 16 条
[1]  
[Anonymous], REARRANGEMENT GROUND
[2]  
Bohne C., 1995, CRC HDB ORGANIC PHOT, P416
[3]  
CHU CS, 1994, SYNLETT, P635
[4]   A formal synthesis of (+/-)-reserpine from methyl vanillate [J].
Chu, CS ;
Liao, CC ;
Rao, PD .
CHEMICAL COMMUNICATIONS, 1996, (13) :1537-1538
[5]   TRICYCLO[3.3.0.02,8]OCTAN-3-ONES - PHOTOCHEMICALLY PREPARED BUILDING-BLOCKS FOR ENANTIOSPECIFIC TOTAL SYNTHESES OF CYCLOPENTANOID NATURAL-PRODUCTS [J].
DEMUTH, M ;
SCHAFFNER, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (11) :820-836
[6]   PHOTOCHEMISTRY AND SPECTROSCOPY OF BETA, GAMMA-UNSATURATED CARBONYL-COMPOUNDS [J].
HOUK, KN .
CHEMICAL REVIEWS, 1976, 76 (01) :1-74
[7]   Short and efficient route to substituted linear triquinanes from 2-methoxyphenols [J].
Hsu, DS ;
Rao, PD ;
Liao, CC .
CHEMICAL COMMUNICATIONS, 1998, (17) :1795-1796
[8]   Stereoselective synthesis of highly substituted and oxygenated cis-decalins [J].
Hsu, PY ;
Lee, YC ;
Liao, CC .
TETRAHEDRON LETTERS, 1998, 39 (07) :659-662
[9]   CHEMISTRY OF BENZOQUINONES AND MASKED BENZOQUINONES .13. SYNTHESIS OF ANGULARLY AND LINEARLY FUSED TRIQUINANES VIA THE COMMON INTRAMOLECULAR DIELS-ALDER ADDUCT OF A MASKED ORTHO-BENZOQUINONE [J].
HWANG, JT ;
LIAO, CC .
TETRAHEDRON LETTERS, 1991, 32 (45) :6583-6586
[10]   Synthesis of bicyclo[4.1.0]hept-2-enes (trinorcarenes) by photochemical reaction of bicyclo[2.2.2]oct-5-en-2-ones [J].
Katayama, S ;
Hiramatsu, H ;
Aoe, K ;
Yamauchi, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04) :561-576