CHEMISTRY OF ORTHO-BENZOQUINONES .3. REACTIONS WITH FURANS AND AN ISOBENZOFURAN

被引：37

作者：

HORSPOOL, WM

TEDDER, JM

DIN, ZU

机构：

[1] Department of Chemistry, The University

[2] Department of Chemistry, The University, St. Andrews

来源：

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 13期

关键词：

D O I：

10.1039/j39690001694

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of tetrachloro-1,2-benzoquinone and 1,2-benzoquinone with furan, 2-methylfuran, and 2,5-diphenylfuran are reported. Dihydrofurobenzodioxin adducts are isolated in most cases. The reaction of 1,2-benzoquinone with 2-methylfuran is shown to be solvent dependent; in the presence of a trace of ethanol, addition of ethanol to the dihydrofurobenzodioxin takes place. A two-step mechanism is proposed and exemplified by the observed ring-opening reaction of the quinones with an isobenzofuran.

引用

页码：1694 / &

共 17 条

[1] ADAMS R, 1946, J AMER CHEM SOC, V62, P56
[2] ANSELL MF, 1967, TETRAHEDRON LETT, P4537
[3] ANSELL MF, 1965, CHEM COMM, P521
[4] THE DIELS-ALDER REACTION WITH CERTAIN ORTHO-QUINONES
BARLTROP, JA
JEFFREYS, JAD
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JAN): : 154 - 159
[5] ORTHO- QUINONES AS DIENOPHILES
BARLTROP, JA
JEFFREYS, JAD
[J]. EXPERIENTIA, 1951, 7 (08): : 290 - 290
[6] Burgstahler A.W., 1966, ORG SYNTH, V46, P28
[7] CHAPMAN DD, 1966, TETRAHEDRON LETT, P6175
[8] PREPARATION OF DIENE ADDUCTS OF O-QUINONES
EVANS, FJ
WILGUS, HS
GATES, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (05) : 1655 - &
[9] HORNER L, 1950, ANN, V570, P89
[10] REACTION OF O-BENZOQUINONE WITH CYCLOPENTADIENE
HORSPOOL, WM
TEDDER, JM
DIN, ZU
[J]. CHEMICAL COMMUNICATIONS, 1966, (21) : 775 - &

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