European Journal of Organic Chemistry p. 3716 - 3723 (2018)
Update date:2022-07-30
Topics:
Obijalska, Emilia
Pawelec, Maria
Mlostoń, Grzegorz
Capperucci, Antonella
Tanini, Damiano
Heimgartner, Heinz
Isomeric fluorinated α-bromoenones react with dinucleophilic β-mercaptoalcohols in CH2Cl2 at room temperature in the presence of Et3N in a multistep process. Depending on the position of the CF3 group, different O,S-heterocycles or non-cyclic products were obtained. With 3-bromo-1,1,1-trifluorobut-3-en-2-ones derivatives of 1,4-oxathianes were formed, but isomeric 2-bromo-4,4,4-trifluorobut-2-en-1-ones yielded 1,3-oxathiolanes or non-cyclic sulfides. The thia-Michael addition is proposed as the initial step of the reaction, and the final heterocyclization is governed by the location of the CF3 group.
View MoreContact:+86-532-55689660
Address:qingdao
Contact:86-511-85210668 0511-85210668, 85210818, 85210898
Address:Yihai Garden E-902,NO.99 Daxi RD., Zhenjiang Jiiangsu ,China
Yixing Bluwat Chemicals Co., Ltd.
Contact:+86 510 87821568
Address:Yongan Road, Yixing Chemical Industrial Park, Yixing, Jiangsu, China
Contact:0086-29-89196322
Address:North of the Fifth Keji Road, Hi-Tech Industrial Zone, Xi'an City, Shaanxi Province, China
Contact:86-574-26865651
Address:529 YuanBaoShan Road, Beilun District
Doi:10.1002/anie.201408651
(2015)Doi:10.1016/j.tet.2009.02.039
(2009)Doi:10.1021/acs.joc.6b02547
(2017)Doi:10.1246/cl.1988.111
(1988)Doi:10.1002/ejoc.200900083
(2009)Doi:10.1021/ja901140v
(2009)