235418-59-4Relevant academic research and scientific papers
Synthesis of organofluorine compounds using ene type reaction of N-(p-toluenesulfonyl)trifluoroacetaldehyde imine
Kumadaki, Itsumaro,Jonoshita, Shuichi,Harada, Atsuhiro,Omote, Masaaki,Ando, Akira
, p. 61 - 63 (2007/10/03)
N-Tosyltrifluoroacetaldehyde imine (4) reacted as an enophile, but it is very sensitive to moisture and the yields of ene products were low. N-(2,2,2-Trifluoro-1-ethoxyethyl)tosylamide (11), obtained by the reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with tosylamide (3) in the presence of TiCl4 followed by addition of ethanol, was found to react as a good substitute for 4 to give the same products from the ene reaction of 4 in much better yields.
Synthesis of organofluorine compounds using the ene reaction of N-(p- toluenesulfonyl)trifluoroacetaldehyde imine
Jonoshita, Shuichi,Harada, Atsuhiro,Omote, Masaaki,Ando, Akira,Kumadaki, Itsumaro
, p. 656 - 662 (2007/10/03)
N-Tosyltrifluoroacetaldehyde imine (4) reacted with terminal olefins by only heating together to give the ene reaction products. This means the imine is much more reactive than trifluoroacetaldehyde (2) itself as an enophile. However, 4 was very sensitive to moisture and the yields were low even if it was used without isolation. Further, it did not react with non-terminal olefins. In the course on study of the mechanism of this reaction, we found that N-(2,2,2-trifluoro-1-ethoxyethyl)tosylamide (12), obtained by the reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with tosylamide (3) in the presence of titanium(IV) chloride followed by addition of ethanol, reacted in the presence of sodium hydride and titanium(IV) chloride to give the same products from the ene reaction of 4 in much better yields. Interestingly, this reaction proceeded with non-terminal olefins.
