Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid

被引：1

作者：

Mammeri, Oussama Abdelhamid ^{[1
]}

Baranov, Ilia M. ^{[1
]}

Ivanov, Alexandr Yu ^{[2
]}

Boyarskaya, Irina A. ^{[1
]}

Vasilyev, Aleksander. V. ^{[1
,3
]}

机构：

[1] St Petersburg State Univ, Inst Chem, 7-9 Univ Nab, St Petersburg 199034, Russia

[2] St Petersburg State Univ, Ctr Magnet Resonance, Res Pk, Univ Pr 26, St Petersburg 198504, Petrodvoretz, Russia

[3] St Petersburg State Forest Tech Univ, Dept Chem, Inst Per 5, St Petersburg 194021, Russia

来源：

TETRAHEDRON | 2023年 / 146卷

关键词：

Allene carboxylates; Furanones; Triflic acid; Carbocations; Electrophilic activation; ESTERS; 2,3-ALLENOATES; BUTENOLIDES; INVOLVEMENT; IODINATION; GENERATION; CHEMISTRY; DIENES; ACCESS; IONS;

D O I：

10.1016/j.tet.2023.133649

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkyl allene carboxylates [R2(R3)C=C=C(R1)-C(=O)OAlk] in Bronsted superacid CF3SO3H (triflic acid, TfOH) at room temperature or 70 degrees C for 30 min are cyclized to form 2-(5H)-furanones in yields up to 83%. The reaction cationic intermediates, O-monoprotonated [R2(R3)C=C=C(R1)-C(=O+H)OAlk] and O,C-diprotonated [R2(R3) C+-CH=C(R1)-C(=O+H)OAlk] forms of starting allenes, have been studied experimentally by NMR and theoretically by DFT calculations. It has been found that the cyclization proceeds via O,C-diprotonated forms of starting allenes.

引用

页数：8

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