US EPA

2872340 

Journal Article 

Reactions of 2,2-bis(trifluoromethyl)oxirane with alcohols under phase transfer catalysis 

Petrov, VA 

2004 

Yes 

Journal of Fluorine Chemistry
ISSN: 0022-1139
EISSN: 1873-3328 

125 

4 

531-536 

English 

10.1016/j.jfluchem.2003.11.026 

WOS:000221629100008 

It was demonstrated that the reaction of 2,2-bis(trifluoromethyl)oxirane (1) with variety of alcohols could be successfully carried out under phase transfer catalysis conditions using sodium or potassium hydroxide as a base. For example, reaction of CH3OH, C2 H5OCH2CH2OH, HOCH2 CH2OH with one or two moles of 1 in the presence of the catalyst [(C4H9)4 N+ HSO4-] gives the corresponding tertiary alcohols R[OCH2C(CF3)2OH] n (n=1 or 2) in 43-53% yield, along with some O[CH2 C(CF3)2OH]2. Benzyl alcohol and phenol under similar conditions are less active, producing in the reaction with 1 the corresponding adducts ArOCH2C(CF3) 2OH in 31-35% yield. Fluorinated alcohols, such as CF3CH2OH, ClCF2CH2OH, HCF2CF2CH2OH have much higher reactivity towards 1 giving ring opening products in 82-97% yield. Even in the reaction of hindered hexafluoro- iso -propanol the corresponding adduct was isolated in 43% yield. Surprisingly, the reaction of iso-propanol and epoxide 1, results in the formation of O[CH2C(CF3)2OH]2 as a major product, isolated in 56% yield. Possible mechanism for the formation of the last product was proposed. © 2004 Elsevier B.V. All rights reserved. 

phase transfer catalysis; 2,2-bis(trifluoromethyl)oxirane; alcohols; fluorinated alcohols