Chemical and Pharmaceutical Bulletin p. 656 - 662 (1999)
Update date:2022-08-05
Topics:
Jonoshita, Shuichi
Harada, Atsuhiro
Omote, Masaaki
Ando, Akira
Kumadaki, Itsumaro
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.
View MoreHubei Xiangxi Chemical Industry Co.,Ltd
Contact:+86-710-3454830
Address:No.7, Daqing East Road, Xiangfan City, Hubei Province, China
Contact:+86-21-54391580
Address:Room 502,No.65,Lane 2388 Hongxin Road,Shanghai,China
Hangzhou yi lu biont technology Co., LTD
Contact:+86-571-88152630
Address:Hangzhoushi HuafengRoad Yicheng3Building1001room.
website:http://www.vanzpharm.com/en/index.html
Contact:86-27-84492310
Address:FANHU INDUSTRY PARK
Lyrin Industrial Corporation Limited
Contact:86-731-82571800
Address:Rm 2408,Asia Economy International Building,Shaoshan Road South,Yuhua District,Changsha,Hunan,China
Doi:10.1007/BF00474348
(1986)Doi:10.1039/d1cc02257a
(2021)Doi:10.1016/S0040-4020(99)00425-1
(1999)Doi:10.1021/ja01226a011
(1945)Doi:10.1039/j39690001935
(1969)Doi:10.1007/BF02496219
(1997)
