136808-13-4Relevant academic research and scientific papers
Ene-type reaction of trifluoroacetaldehyde hemiacetal with ene compounds in the presence of a Lewis acid
Sakumo, Kunihiro,Kuki, Noriko,Kuno, Terumi,Takagi, Toshiyuki,Koyama, Mayumi,Ando, Akira,Kumadaki, Itsumaro
, p. 165 - 170 (2007/10/03)
Reaction of trifluoroacetaldehyde ethyl hemiacetal with ene compounds in the presence of a Lewis acid gives α-trifluoromethylated homoallyl alcohols, the same products as those from the ene reaction of trifluoroacetaldehyde, in moderate to good yields. Boron trifluoride etherate was found to be most effective in this reaction. This method eliminated many difficulties encountered on the ene reaction of trifluoroacetaldehyde, which is a gas at room temperature and polymerizes to insoluble polymer in the presence of a Lewis acid.
Studies on trifluoromethyl ketones. VII. Ene reaction of trifluoroacetaldehyde and its application for synthesis of trifluoromethyl compounds
Ogawa,Nagai,Nonomura,Takagi,Koyama,Ando,Miki,Kumadaki
, p. 1707 - 1712 (2007/10/02)
As an extension of our studies on the ene reaction of trifluoromethyl ketones, the ene reaction of trifluoroacetaldehyde was examined. The aldehyde reacted with various ene compounds as a good enophile in the presence of Lewis acids, among which methylaluminum dichloride worked best, though polymerization of the aldehyde caused by the Lewis acid often lowered the isolation yields of the ene reaction. The ene reaction products were successfully oxidized to trifluoromethyl β,γ-unsaturated ketones with Dess-Martin reagent. Reduction of the ene reaction products followed by oxidation with Jones reagent gave saturated trifluoromethyl ketones. The β,γ-unsaturated ketone rearranged on thermolysis to an α,β-unsaturated ketone. These ketones obtained were converted to other types of trifluoromethyl compounds. Thus, the ene reaction of trifluoroacetaldehyde provides a versatile method for synthesis of many types of trifluoromethyl compounds. During the derivatization, a trifluoromethyl group was found to behave as a much larger substituent than a decyl group.
