BORON COMPOUND AS A TRAPPING REAGENT OF ALPHA-HYDROXY O-QUINODIMETHANES IN THE DIELS-ALDER REACTION

被引：23

作者：

SHIMADA, S ^{[1
]}

OSODA, K ^{[1
]}

NARASAKA, K ^{[1
]}

机构：

[1] UNIV TOKYO, FAC SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1993年 / 66卷 / 04期

关键词：

D O I：

10.1246/bcsj.66.1254

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Diels-Alder reaction of methyl 4-hydroxy-2-butenoate and alpha-hydroxy o-quinodimethanes, generated from 1,2-dihydrobenzocyclobuten-1-ol derivatives by thermolysis, proceeds by the use of phenylboronic acid as a template. Boron reagents trap an alpha-hydroxy o-quinodimethane (5-methylene-6-(1-hydroxyalkylidene)-1,3-cyclohexadiene) generated photochemically from o-tolualdehyde and the Diels-Alder reaction with methyl 4-hydroxy-2-butenoate occurs to give the cycloadducts.

引用

页码：1254 / 1257

页数：4

共 16 条

[1] ARNOLD BJ, 1974, J CHEM SOC PERK T 1, P415, DOI 10.1039/p19740000415
[2] BLOMQUIST AT, 1960, TETRAHEDRON LETT, P13
[3] PROTON NMR-SPECTRA OF 1-SUBSTITUTED BENZOCYCLOBUTENES (BICYCLO[4,2,0]OCTA-1,3,5-TRIENES)
BUBB, WA
STERNHELL, S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (08) : 1685 - 1697
[4] CONDENSED CYCLOBUTANE AROMATIC SYSTEMS .2. DIHALO DERIVATIVES OF BENZOCYCLOBUTENE AND BENZOCYCLOBUTADIENE DIMER
CAVA, MP
NAPIER, DR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (07) : 1701 - 1705
[5] CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .8. THE MECHANISM OF FORMATION OF 1,2-DIBROMOBENZOCYCLOBUTENE - A NEW DIELS-ALDER SYNTHESIS
CAVA, MP
DEANA, AA
MUTH, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (24) : 6458 - 6460
[6] THE INTRAMOLECULAR DIELS-ALDER REACTION - RECENT ADVANCES AND SYNTHETIC APPLICATIONS
FALLIS, AG
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02): : 183 - 234
[7] Fleming I, 1976, FRONTIER ORBITALS OR, P121
[8] ARYLBORONIC ACIDS .4. REACTIONS OF BORONOPHTHALIDE
LENNARZ, WJ
SNYDER, HR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (09) : 2172 - 2175
[9] NARASAKA K, 1991, SYNTHESIS-STUTTGART, P1171
[10] MONOMERIC DIALKYLBORANES
NEGISHI, E
KATZ, JJ
BROWN, HC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (11) : 4025 - &

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