75415-89-3Relevant academic research and scientific papers
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.
VINYLIODONIUM SALTS: THEIR STEREOSPECIFIC SYNTHESIS AND REACTIONS AS THE ACTIVATED VINYL HALIDES
Ochiai, Masahito,Sumi, Kenzo,Nagao, Yoshimitsu,Fujita, Eiichi
, p. 2351 - 2354 (2007/10/02)
Vinyliodonium salts 2 were synthesized from vinylsilanes 1 by the reaction with iodosylbenzene and triethyloxonium tetrafluoroborate.The reaction occurs stereospecifically with retention of configuration.Vinyliodonium salts 2 are highly effective as the activated species of vinyl iodides.Thus, a variety of substituted olefins including α-cyano and α-nitro olefins, vinyl sulfides, vinyl halides, and α,β-unsaturated esters, were prepared from 2 under mild reaction conditions.
NITRODESTANNYLATION. A NEW SYNTHESIS OF CONJUGATED NITRO CYCLO OLEFINS
Corey, E. J.,Estreicher, Herbert
, p. 1113 - 1116 (2007/10/02)
A new process for the conversion of cyclic ketones to 1-nitro olefines, as outlined in eq. 2 below, is described.
