Conversion of (Z)-1,4-dihydroxyalk-2-enes into 2,5-dihydrofurans and of alkane-1,4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas formed by their copper(I)-mediated reactions with dicyclohexylcarbodiimide

被引：18

作者：

Duffy, MG ^{[1
]}

Grayson, DH ^{[1
]}

机构：

[1] Univ Dublin Trinity Coll, Chem Lab, Dublin 2, Ireland

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 13期

关键词：

D O I：

10.1039/b203389p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Z)-1,4-Dihydroxyalk-2-enes react with dicyclohexylcarbodiimide in the presence of catalytic amounts of copper(I) chloride to give O-alkyl monoisoureas which cyclise to give 2-substituted-2,5-dihydrofurans and dicyclohexylurea when they are treated with trifluoroacetic acid. Alkane-1,4-diols likewise give O-alkyl monoisoureas which cyclise to yield tetrahydrofurans.

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页码：1555 / 1563

页数：9

相关论文

共 41 条

[1] REACTION OF O18-LABELED ETHANOL WITH PHENOLS AND N,N]-DICYCLOHEXYLCARBODIIMIDE [J].

BACH, FL .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :1300-&

[2] TRIPHENYLPHOSPHINE-TETRACHLOROMETHANE PROMOTED CHLORINATION AND CYCLODEHYDRATION OF SIMPLE DIOLS [J].

BARRY, CN ;

EVANS, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) :3361-3364

[3] CYCLODEHYDRATION AND CHLORINATION OF SIMPLE DIOLS WITH TRIPHENYLPHOSPHINE AND TERT-BUTYL HYPOCHLORITE [J].

BARRY, CN ;

EVANS, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (17) :2825-2828

[4] SYNTHESIS OF 2,5-DIHYDROFURANS FROM ALPHA-ALLENIC ALCOHOLS [J].

BEAULIEU, PL ;

MORISSET, VM ;

GARRATT, DG .

TETRAHEDRON LETTERS, 1980, 21 (02) :129-132

[5] OPTICALLY-ACTIVE 5-MEMBERED OXYGEN-CONTAINING RINGS - A SYNTHESIS OF (+)-ELDANOLIDE [J].

BLOCH, R ;

SECK, M .

TETRAHEDRON, 1989, 45 (12) :3731-3740

[6] Reactions of some substituted divinylacetylenes [J].

Blomquist, AT ;

Marvel, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :1655-1662

[7] TOTAL SYNTHESIS OF DL-CERULENIN [J].

BOECKMAN, RK ;

THOMAS, EW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (04) :987-994

[8] OXIDATION OF ACETYLENES WITH TERT-BUTYL HYDROPEROXIDE CATALYZED BY SELENIUM DIOXIDE - ALPHA,ALPHA'-DIOXYGENATION OF INTERNAL ALKYNES [J].

CHABAUD, B ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4202-4204

[9] EFFICIENT TRANSFORMATION OF (Z)-2-BUTENE-1,4-DIOLS TO ALPHA, BETA-BUTENOLIDES - A SIMPLE SYNTHESIS OF (+/-)-ELDANOLIDE [J].

CHAKRABORTY, TK ;

CHANDRASEKARAN, S .

TETRAHEDRON LETTERS, 1984, 25 (27) :2891-2894

[10] OXYGEN YLIDES .1. REACTIONS OF CARBENES WITH OXETANE [J].

FRIEDRICH, K ;

JANSEN, U ;

KIRMSE, W .

TETRAHEDRON LETTERS, 1985, 26 (02) :193-196

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