- Synthesis, structure, and thermolysis of a novel spirotellurane bearing two 1,2-oxatelluretane rings, 1,5-dioxa-4λ4-telluraspiro[3.3]heptane: Oxirane and olefin formation reactions
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The first 1,5-dioxa-4λ4-telluraspiro[3.3]heptane was synthesized and its structure was determined by X-ray analysis. This tellurane gave the corresponding oxirane and olefin, as well as alcohol, upon heating, which were shown to be formed via a radical pathway.
- Kano, Naokazu,Takahashi, Tatsuhisa,Kawashima, Takayuki
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- Friedel-Crafts alkylations of arenes with mono- and bis(trifluoromethyl) oxiranes in superacid medium: Facile synthesis of α-(trifluoromethyl)- and α,α-bis(trifluoromethyl)-β-arylethanols
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Triflic acid catalyzed Friedel-Crafts alkylation of aromatics with mono- and bis(trifluoromethyl)oxiranes through ring opening afforded α-(trifluoromethyl) and α,α-bis(trifluoromethyl)-β- phenylethanols in excellent yields. The regioselectivity of the oxirane ring opening and subsequent Friedel-Crafts alkylation have been found to depend on the electronic and steric effects of the substituents in the oxirane ring. DFT studies show that C2-O bond is longer than C1-O bond due to high electron-withdrawing effect of CF3 groups effecting C2-O cleavage resulting in a C2 electrophilic center promoting electrophilic substitution with the C2 center on aromatics. Georg Thieme Verlag Stuttgart.
- Prakash, G. K. Surya,Linares-Palomino, Pablo J.,Glinton, Kevin,Chacko, Sujith,Rasul, Golam,Mathew, Thomas,Olah, George A.
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p. 1158 - 1162
(2008/03/13)
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- Synthesis of polyfluorinated tertiary alcohols using ring opening reactions of 2,2-bis(trifluoromethyl)oxirane
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This paper describes new reactions of 2,2-bis(trifluoromethyl)oxirane (1). Ring opening of 1 by oxygen, nitrogen, sulfur or carbon nucleophiles (Nu-) proceeds regioselectively, with exclusive formation of tertiary alcohols: NuCH2C(CF3)2OH. The reaction of 1 with strong acids (HX) is also regioselective and proceeds under mild conditions leading to the formation of XCH2C(CF3)2OH (X = FSO2O, CF3SO2O, Cl, I). The addition of acetic acid to 1, however, requires an elevated temperature and TaF5 a catalyst. Highly selective reactions of 1 with nucleophilic or electrophilic reagents provide a simple and general route to materials containing CH2C(CF3)2OH group.
- Petrov, Viacheslav A.
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p. 2225 - 2231
(2007/10/03)
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- Synthesis and thermolysis of novel spiroselenuranes bearing two oxaselenetane rings: Double oxirane formation reactions from 1,5-dioxa-4λ4-selenaspiro[3.3]heptanes
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The first stable spiroselenuranes bearing two oxaselenetane rings have been synthesized, characterized by X-ray crystallographic analysis, and shown to be thermally reactive giving two molar equivalents of the corresponding oxirane with elimination of ele
- Ohno,Kawashima,Okazaki
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p. 463 - 464
(2007/10/03)
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