A MOLECULAR ORBITAL CALCULATION STUDY ON THE INTERESTING REACTIVITY OF FLUORINE-CONTAINING 3,4-DIHYDRO-2H-PYRANS WITH AROMATIC COMPOUNDS IN THE PRESENCE OF TRIFLUOROACETIC ACID

被引：3

作者：

Ota, Norio ^{[1
]}

Kamitori, Yasuhiro ^{[2
]}

Nishiguchi, Eisuke ^{[2
]}

Ishii, Makoto ^{[3
]}

Okada, Etsuji ^{[2
]}

机构：

[1] Kobe Univ, Grad Sch Sci & Technol, Nada Ku, Kobe, Hyogo 6578501, Japan

[2] Kobe Univ, Grad Sch Engn, Dept Sci & Chem Engn, Nada Ku, Kobe, Hyogo 6578501, Japan

[3] Kobe Univ, Fac Engn, Dept Sci & Chem Engn, Nada Ku, Kobe, Hyogo 6578501, Japan

来源：

HETEROCYCLES | 2011年 / 82卷 / 02期

关键词：

Fluorine-Containing Heterocycle; Dihydropyran; Trifluoroacetic Acid; Pyrylium; Molecular Orbital Calculation; FACILE SYNTHESIS; ETHERS;

D O I：

10.3987/COM-10-S(E)82

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 6-trifluoromethyl-3,4-dihydro-2H-pyrans (1) with aromatic compounds in trifluoroacetic acid gave 4-arylated dihydropyrans (3) selectively, whereas that of 5-trifluoroacetyl-6-trifluoromethyl-3,4-dihydro-2H-pyrans (2) with aromatic compounds in refluxing trifluoroacetic acid afforded the ring-opening products (4) via exclusive attack of aromatic compounds at the 2-position of 2. These two interesting reactions affording the quite different products from the similar substrates were elucidated on the basis of DFT calculations.

引用

页码：1337 / +

页数：8

共 3 条

[1] A MOLECULAR ORBITAL CALCULATION STUDY ON RING-OPENING REACTIONS OF FLUORINE-CONTAINING 3,4-DIHYDRO-2H-PYRANS WITH AMINES AND THIOLS
Ota, Norio
Kamitori, Yasuhiro
Tamai, Yusuke
Feng, Guo
Hatakenaka, Mizuki
Okada, Etsuji
HETEROCYCLES, 2011, 83 (11) : 2509 - 2516
[2] Synthesis of 3,4-Dihydropyridin-2(1H)-ones and 3,4-Dihydro-2H-pyrans via Four-Component Reactions of Aromatic Aldehydes, Cyclic 1,3-Carbonyls, Arylamines, and Dimethyl Acetylenedicarboxylate
Sun, Jing
Xia, Er-Yan
Wu, Qun
Yan, Chao-Guo
ACS COMBINATORIAL SCIENCE, 2011, 13 (04) : 421 - 426
[3] ONE STEP INTRODUCTION OF 4,4-BIS(TRIFLUOROACETYL)-1,3-BUTADIENE SYSTEM TO AROMATIC RINGS USING FLUORINE-CONTAINING 3,4-DIHYDRO-2H-PYRANS. A FACILE SYNTHETIC METHOD FOR 1,1,1,5,5,5-HEXAFLUORO-3-[(E)-3-ARYLALLYLIDENE]PENTANE-2,4-DIONES
Ota, Norio
Okada, Etsuji
Sonoda, Atsushi
Muro, Nobuyuki
Shibata, Dai
Medebielle, Maurice
HETEROCYCLES, 2008, 76 (01) : 215 - 219

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