ACID CATALYZED ISOMERIZATION OF 7- OXABICYCLO (2.2.1) HEPTADIENE AND OXEPIN DERIVATES

被引：45

作者：

VOGEL, P

WILLHALM, B

PRINZBACH, H

机构：

来源：

HELVETICA CHIMICA ACTA | 1969年 / 52卷 / 03期

关键词：

D O I：

10.1002/hlca.19690520305

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The acid catalyzed isomerization of several substituted oxanorbornadienes 4 and oxepines 10 ‐ easily available from 4 by a photochemical and a consecutive thermal step ‐ allows the synthesis of several highly substituted phenols and 2,4‐cyclohexadienones in a straightforward manner and with good to excellent yields. The formation of the methoxycarbonyl‐hexadienes 18e and 18f upon photolysis of 9e and 17f in methanol supports the structure elucidation. The relative importance of the McLAFFERTY and EMERY effects in the mass spectral degradation of methoxycarbonyl and methyl substituted phenols are discussed. Copyright © 1969 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：584 / &

共 38 条

[1] DIELS-ALDER REACTIONS OF 2-ARYLFURANS
AYRES, DC
SMITH, JR
[J]. CHEMICAL COMMUNICATIONS, 1967, (17) : 886 - &
[2] Metabolism of polycyclic compounds 4. Production of a dihydroxy-1 : 2 : 5 : 6-dibenzanthracene from 1 : 2 : 5 : 6-dibenzanthracene
Boyland, E
Levi, AA
Mawson, EH
Roe, E
[J]. BIOCHEMICAL JOURNAL, 1941, 35 : 184 - 191
[3] DIELS-ALDER ADDUCTS OF DICYANOACETYLENE AND THEIR ELECTRONIC SPECTRA
COOKSON, RC
DANCE, J
GODFREY, M
[J]. TETRAHEDRON, 1968, 24 (03) : 1529 - &
[4] REACTIONS OF FURAN COMPOUNDS .18. NUCLEAR ACETOXYLATION
DALELIO, GF
WILLIAMS, CJ
WILSON, CL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (06) : 1025 - 1028
[5] DAVIDSON WJ, 1968, TETRAHEDRON LETT, P4589
[6] MASS SPECTRA OF AROMATIC ESTERS
EMERY, EM
[J]. ANALYTICAL CHEMISTRY, 1960, 32 (11) : 1495 - 1506
[7] FRANCK RW, 1967, TETRAHEDRON LETT, P1789
[8] GIANNONI M, 1967, THESIS U LAUSANNE
[9] ON MECHANISM OF 2,4-CYCLOHEXADIENONE PHOTOISOMERIZATION
GRIFFITH.J
HART, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (12) : 3297 - +
[10] A NEW GENERAL PHOTOCHEMICAL REACTION OF 2,4-CYCLOHEXADIENONES
GRIFFITHS, J
HART, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) : 5296 - +

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