56569-07-4Relevant academic research and scientific papers
Sm/Sml2/TiCl4(cat.) system promoted direct alkylidenating reaction of ketones with gem-dibromomethyl sulfones: A new method for preparation of alkylidene sulfones
Liu,Zhang,Liu
, p. 472 - 473 (2007/10/03)
Alkylidene sulfones were prepared in moderate to good yields via direct alkylidenating reaction of ketones with geminal dibromomethyl sulfones promoted by the Sm/Sml2 system in the presence of a catalytic amount of TiCl4 under mild conditions.
Stereoselective preparation of vinyl sulfones by protodesilylation of allyl silanes
Funk, Raymond L.,Umstead-Daggett, Joy,Brummond, Kay M.
, p. 2867 - 2870 (2007/10/02)
Allyl sulfones can be conjugated to furnish vinyl sulfones via allyl silane intermediates. The stereoselectivity observed in the protodesilylation step provides a new method for stereoselective preparation of (E)-di-and tri substituted vinyl sulfones.
β-copper(II) ketones. Generation, coupling, and highly stereoselective trapping by electron-deficient acetylenes
Ryu, Ilhyong,Matsumoto, Koichi,Kameyama, Yasuhiro,Ando, Masato,Kusumoto, Nobuo,Ogawa, Akiya,Kambe, Nobuaki,Murai, Shinji,Sonoda, Noboru
, p. 12330 - 12339 (2007/10/02)
The generation and the reaction of β-copper(II) ketones via electrophilic ring opening of siloxycyclopropanes with copper(II) tetrafluoroborate (Cu(BF4)2) were studied. Treatment of siloxycyclopropane with Cu(BF4)2 resulted in desilylative dimerization to give a 1,6-diketone in good yield. The ring opening took place regioselectively across the bond between the methylene and siloxy carbons. The reaction is reasonably interpreted by assuming the electrophilic ring opening by cupric ion to form β-copper(II) ketone and trimethylsilylfluoride, followed by dimerization. With dimethyl acetylene dicarboxylate (DMAD) and water, β-(acyl)alkyls were captured to give dimethyl 2-(3-oxoalkyl)-maleate with high degree of stereoselectivity. The stereoselective transfer of β-(acyl)alkyl arises from syn addition across the triple bond followed by in situ protonation of the resulting vinylcopper species with retention of configuration. The stereoselective transfer of β-(acyl)alkyls to acetylenic sulfones, which gives β-(acyl)alkylated vinylic sulfones, was also successful.
