Fragmentation of trifluoromethylated alkenes and acetylenes by N,N-binucleophiles. Synthesis of imidazolines or imidazolidines (oxazolidines) controlled by substituent.
The reaction of beta-halogeno-beta-polyfluoromethylstyrenes with N,N- or N,O-binucleophiles leads to unexpected fragmentation products (imidazolines) or to heterocyclization giving CF(3)-substituted imidazolidines (N,N-) and oxazolidines (N,O-) depending on aryl substituent. The scope and the reaction mechanism are discussed.
Nenajdenko
Valentine G
VG
Department of Chemistry, Moscow State University, Leninskie Gory, Moscow 119992, Russia. nen@acylium.chem.msu.ru
Muzalevskiy
Vasiliy M
VM
Shastin
Aleksey V
AV
Balenkova
Elizabeth S
ES
Kondrashov
Evgeniy V
EV
Ushakov
Igor A
IA
Rulev
Alexander Yu
AY
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D048288:Imidazolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D048289:Imidazolidines; D048288:Imidazolines