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

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 09期

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

页码：801 / 802

页数：2

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
Chu, CS
Liao, CC
Rao, PD
[J]. 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
DEMUTH, M
SCHAFFNER, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (11) : 820 - 836
[6] PHOTOCHEMISTRY AND SPECTROSCOPY OF BETA, GAMMA-UNSATURATED CARBONYL-COMPOUNDS
HOUK, KN
[J]. CHEMICAL REVIEWS, 1976, 76 (01) : 1 - 74
[7] Short and efficient route to substituted linear triquinanes from 2-methoxyphenols
Hsu, DS
Rao, PD
Liao, CC
[J]. CHEMICAL COMMUNICATIONS, 1998, (17) : 1795 - 1796
[8] Stereoselective synthesis of highly substituted and oxygenated cis-decalins
Hsu, PY
Lee, YC
Liao, CC
[J]. 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
HWANG, JT
LIAO, CC
[J]. 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
Katayama, S
Hiramatsu, H
Aoe, K
Yamauchi, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 561 - 576

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