Cyclodimerization and Diels-Alder reaction of a spiroepoxycyclohexadienone with an o-quinodimethane structure

被引：9

作者：

Bonnarme, V

Mondon, M

Cousson, A

Gesson, JP

机构：

[1] Univ Poitiers, Lab Chim 7, F-86022 Poitiers, France

[2] CNRS, F-86022 Poitiers, France

[3] CE Saclay, Lab Leon Brillouin, F-91191 Gif Sur Yvette, France

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 12期

关键词：

D O I：

10.1039/a901914f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of 3-hydroxymethyl-2-naphthol with periodate affords a single exo-syn dimer arising from the intermediate ortho quinonoid spiroepoxycyclohexadienone; the latter can also be trapped by reactive dienophiles.

引用

页码：1143 / 1144

页数：2

共 24 条

[1] PERIODATE OXIDATION OF PHENOLS .9. OXIDATION OF ORTHO (OMEGA-HYDROXYALKYL) PHENOLS [J].

ADLER, E ;

BRASEN, S ;

MIYAKE, H .

ACTA CHEMICA SCANDINAVICA, 1971, 25 (06) :2055-&

[2] PERIODATE OXIDATION OF PHENOLS .11. DIELS-ALDER REACTIONS OF 2,4-CYCLOHEXADIENONES .1. STRUCTURAL AND STERIC ORIENTATION IN DIMERIZATION OF 2,4-CYCLOHEXADIENONES [J].

ADLER, E ;

HOLMBERG, K .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (04) :465-472

[3] Unusual stereoselectivity in Diels-Alder cycloadditions of 5-bromopyrone [J].

Afarinkia, K ;

Daly, NT ;

GomezFarnos, S ;

Joshi, S .

TETRAHEDRON LETTERS, 1997, 38 (13) :2369-2372

[4] THE SYNTHESIS OF A CONFORMATIONALLY RIGID CALCIUM-CHANNEL BLOCKER [J].

BARRISH, JC ;

SPERGEL, SH ;

MORELAND, S ;

HEDBERG, SA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (01) :95-98

[5]

BARTLETT PA, 1980, TETRAHEDRON, V36, P3

[6] 2-BENZOPYRAN-3-ONE [J].

BLEASDALE, DA ;

JONES, DW ;

MAIER, G ;

REISENAUER, HP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (19) :1095-1096

[7] ORTHOQUINODIMETHANES [J].

CHARLTON, JL ;

ALAUDDIN, MM .

TETRAHEDRON, 1987, 43 (13) :2873-2889

[8] ASYMMETRIC INDUCTION AND [2+1] CYCLOADDITIONS .3. DIASTEREOSELECTIVE EPOXIDATIONS OF SECONDARY ALPHA ETHYLENIC ALCOHOLS AND STEREODIRECTED SYNTHESES OF ALPHA EPOXY ALCOHOLS [J].

CHAUTEMPS, P ;

PIERRE, JL .

TETRAHEDRON, 1976, 32 (05) :549-557

[9] THE [4 + 4] DIMERIZATION OF 2,3-DIMETHYLENE-2,3-DIHYDROFURAN - SECONDARY DEUTERIUM KINETIC ISOTOPE EFFECT EVIDENCE FOR A 2-STEP MECHANISM [J].

CHOU, CH ;

TRAHANOVSKY, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (14) :4138-4144

[10]

FISHWICK CWG, 1988, CHEM QUINONOID COMPO, V2, P403

← 1 2 3 →