119061-96-0Relevant academic research and scientific papers
A regio- and stereoselective entry to (Z)-β-halo alkenyl sulfides and their applications to access stereodefined trisubstituted alkenes
Liu, Ge,Kong, Lichun,Shen, Ji,Zhu, Gangguo
, p. 2310 - 2321 (2014/04/03)
A mild and efficient preparation of (Z)-β-halo alkenyl sulfides via the K2CO3-promoted hydrothiolation of haloalkynes has been realized, producing (Z)-β-bromo and (Z)-β-chloro vinylic sulfides in high yields with excellent regio- and
REACTIONS OF VINYLSILANES WITH LEWIS ACID-ACTIVATED IODOSYLBENZENE: STEREOSPECIFIC SYNTHESIS OF VINYLIODONIUM TETRAFLUOROBORATES AND THEIR REACTIONS AS HIGHLY ACTIVATED VINYL HALIDES
Ochiai, Masahito,Sumi, Kenzo,Takaoka, Yoshikazu,Kunishima, Munetaka,Nagao, Yoshimitsu,et al.
, p. 4095 - 4112 (2007/10/02)
Alkenyl(phenyl)iodonium tetrafluoroborates 3 were synthesized from alkenylsilanes 1 by the reaction with iodosylbenzene and boron trifluoride-diethyl ether or triethyloxonium tetrafluoroborate.The reaction proceeds stereospecifically with retention of configuration of 1.X-ray diffraction analysis of (4-tert-butylcyclohexenyl)phenyliodonium tetrafluoroborate (3b) revealed the highly ionic structure with the distorted T-shape arrangement.Iodonium salts 3 behave like the highly activated species of vinyl iodides due to the high leaving ability of the iodine(III) substituents.Thus, a variety of substituted olefins including α-cyano and α-nitro olefins, vinyl sulfides, vinyl halides and α,β-unsaturated esters, were synthesized from 3 under mild conditions.A ligand coupling mechanism via the formation of 10-I-3 intermediate 27 containing a copper(III) ligand is proposed for the substitutions of 3 with nucleophiles.
