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.
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