An efficient catalytic method for fulvene synthesis

被引：45

作者：

Coskun, Necdet ^{[2
]}

Erden, Ihsan ^{[1
]}

机构：

[1] San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA

[2] Uludag Univ, Dept Chem, TR-16059 Bursa, Turkey

来源：

TETRAHEDRON | 2011年 / 67卷 / 45期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

Fulvenes; LFER studies; Green synthesis; Catalysis; Cyclopentadiene; DIELS-ALDER REACTIONS; ALLENE OXIDE; EXCEPTIONALLY SIMPLE; SINGLET OXYGEN; CHEMISTRY; ENDOPEROXIDES; RESONANCE;

D O I：

10.1016/j.tet.2011.09.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effects of the nature and amount of base, substrate structure, amount of added water and solvent on the condensation of carbonyl compounds with cyclopentadiene in the presence of secondary amines were investigated. Based on these studies, a new efficient and green synthesis of fulvenes was developed. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：8607 / 8614

页数：8

共 40 条

[1] Synthesis and characterization of chlorovinylcyclopentadienyl lanthanides [J].

Alves, NP ;

Maia, AD ;

de Oliveira, W .

JOURNAL OF ALLOYS AND COMPOUNDS, 2000, 303 :178-181

[2] FULVENES AND SUBSTITUTED FULVENES [J].

BERGMANN, ED .

CHEMICAL REVIEWS, 1968, 68 (01) :41-&

[3] Reversible Diels-Alder reactions for the generation of dynamic combinatorial libraries [J].

Boul, PJ ;

Reutenauer, P ;

Lehn, JM .

ORGANIC LETTERS, 2005, 7 (01) :15-18

[4] An imidazolidin-1-ol, nitrone and oxadiazinane ring-chain-ring tautomeric dynamic combinatorial library [J].

Coskun, Necdet ;

Aksoy, Cagdas .

TETRAHEDRON LETTERS, 2009, 50 (25) :3008-3012

[5]

Day J. H, 1963, CHEM REV, V53, P167

[6] CHEMISTRY OF SINGLET OXYGEN - SYNTHESIS OF FUNCTIONALIZED CYCLOPENTENONES FROM SATURATED FULVENE ENDOPEROXIDES [J].

ERDEN, I ;

XU, FP ;

DRUMMOND, J ;

ALSTAD, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3611-3612

[7] Sigmatropic shifts in allene oxide rearrangements: First general route to [3,4] shifts in aliphatic systems [J].

Erden, I ;

Xu, FP ;

Cao, WG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1516-1518

[8] SCOPE AND LIMITATIONS OF FULVENE SYNTHESES - PREPARATION OF 6-VINYL-SUBSTITUTED AND 6-VINYL-FUNCTIONALIZED FULVENES - FIRST EXAMPLES OF NUCLEOPHILIC-SUBSTITUTION ON A 6-(CHLOROMETHYL)FULVENE [J].

ERDEN, I ;

XU, FP ;

SADOUN, A ;

SMITH, W ;

SHEFF, G ;

OSSUN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :813-820

[9] THERMAL-DECOMPOSITION OF 7-ISOPROPYLIDENE-2,3-DIOXABICYCLO[2.2.1]HEPTANE - EVIDENCE FOR ALLENE OXIDE AND CYCLOPROPANONE INTERMEDIATES [J].

ERDEN, I ;

AMPUTCH, MA .

TETRAHEDRON LETTERS, 1987, 28 (33) :3779-3782

[10] CHEMISTRY OF SINGLET OXYGEN - ISOLATION AND CHARACTERIZATION OF A STABLE ALLENE OXIDE FROM A FULVENE ENDOPEROXIDE [J].

ERDEN, I ;

DRUMMOND, J ;

ALSTAD, R ;

XU, FP .

TETRAHEDRON LETTERS, 1993, 34 (08) :1255-1258

← 1 2 3 4 →