Synthesis of 2-fluoro-3-phenylthio-1,3-butadiene and 2-trifluoromethyl-3-phenylthio-1,3-butadiene and their reactivities toward various dienophiles.
A general approach for the synthesis of novel 2-fluoro-3-phenylthio-1,3-butadiene (8) and 2-trifluoromethyl-3-phenylthio-1,3-butadiene (9) from monobromoalkene and dibromoalkenes has been developed. Subsequent Diels-Alder reactions of these dienes with symmetrical and unsymmetrical dienophiles in the presence of Lewis acids gave a variety of fluorinated six-membered carbocycles in moderate to high yields.
Kamaldeep
Paul
P
Department of Chemistry and Medical Chemistry, Yonsei University, Wonju 220-710, Korea.
Hwang
Ji Hye
JH
Choi
Ji Hoon
JH
Jeong
In Howa
IH
D002070:Butadienes / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D006863:Hydrogen-Ion Concentration; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
C545744:2-fluoro-3-phenylthio-1,3-butadiene; C545745:2-trifluoromethyl-3-phenylthio-1,3-butadiene; D002070:Butadienes; D013440:Sulfides