Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes

被引：16

作者：

Bentabed-Ababsa, Ghenia ^{[1
,2
]}

Hamza-Reguig, Samira ^{[1
]}

Derdour, Aicha ^{[1
]}

Domingo, Luis R. ^{[3
]}

Saez, Jose A. ^{[3
]}

Roisnel, Thierry ^{[4
]}

Dorcet, Vincent ^{[4
]}

Nassar, Ekhlass ^{[5
]}

Mongin, Florence ^{[2
]}

机构：

[1] Univ Oran, Fac Sci, Lab Synth Organ Appl, Oran 31000, Algeria

[2] Univ Rennes 1, UMR CNRS 6226, Inst Sci Chim Rennes, Equipe Chim & Photon Mol, F-35042 Rennes, France

[3] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

[4] Univ Rennes 1, UMR CNRS 6226, Inst Sci Chim Rennes, Ctr Diffractometrie 10, F-35042 Rennes, France

[5] Ain Shams Univ, Fac Women Arts Sci & Educ, Dept Chem, Cairo, Egypt

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 42期

关键词：

ELECTRON LOCALIZATION FUNCTION; DIELS-ALDER REACTION; 1,3-DIPOLAR CYCLOADDITION; LEWIS-ACID; QUANTITATIVE CHARACTERIZATION; GEM DICYANOEPOXIDES; CATASTROPHE-THEORY; REACTIVITY; STEREOCHEMISTRY; OPTIMIZATION;

D O I：

10.1039/c2ob26442k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and alkynes (phenylacetylene, methyl propiolate, methyl but-2-ynoate and methyl 3-phenylpropiolate) to give substituted 2,5-dihydrofurans was investigated. The effect of indium(III) chloride on the outcome of the reaction was studied in the case of phenylacetylene and methyl propiolate. The thermal reaction between the carbonyl ylide coming from 2,2-dicyano-3-phenyloxirane and both methyl propiolate and methyl but-2-ynoate was theoretically investigated using DFT methods in order to explain the reactivity and regioselectivity observed.

引用

页码：8434 / 8444

页数：11

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