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
收藏
页码：1337 / +
页数：8
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