Electrophilically-induced cyclodestannylation reactions

Synthesis and characterization of some organo-all-tin dendrimers with different peripheral substituents

“…In contrast, hydrostannation of tetrabutenylstannane (1) [22] succeeded, resulting in the formation of tetrakis(4-triphenylstannylbutyl)stannane (2), which could be isolated after 24 h stirring of a mixture of 1 and a fourfold amount of Ph 3 SnH in 94% yield (Scheme 1).…”

“…Since aryl substituted organotin compounds cause larger J( 13 C,Sn) coupling constants then those of alkyl substituted compounds, the signal at d = 31.77 ppm with 3 J( 13 C 119 Sn) = 63. 22 Hz indicates a c-position for the phenyl substituted peripheral tin atoms and allows an assignment of this signal to the carbon atom in c-position to the phenyl substituted tin atom. The resonance at 31.36 ppm ( 3 J( 13 C 119 Sn) = 57.77 Hz) belongs to the remaining carbon atom.…”

Free-radical chain reactions of organic mercury and tin compounds

“…77) [145]. The initial stage of this CHg = CHCHgCHgSnBUg + e"^ >• CH^E + Bu^Sn"'" (77) reaction is thought to involve addition of electrophiles to the double 3 bond of the A -butenyl ligand to form electron deficient carbon atom 6 to tin.…”

“…The initial stage of this CHg = CHCHgCHgSnBUg + e"^ >• CH^E + Bu^Sn"'" (77) reaction is thought to involve addition of electrophiles to the double 3 bond of the A -butenyl ligand to form electron deficient carbon atom 6 to tin. These incipient carbonium ions then electrophilically induce heterolytic fragmentations of the carbon-tin bond with concurrent ring formation [145]. is more capable than the a-position for accepting a hydrogen atom, it seems that if a 1,2-hydrogen shift were to occur, it would be most reasonable to expect it to yield PhSCHgCHgÔHCHgSnBug rather than PhSCH2CH=CHCH2.…”

“…Tri-n-butyl-A -butenyltin was prepared following a literature pro cedure [76]. Cyclopropylcarbinyl phenyl sulfide was prepared from the reaction of tri-n-butyl-A -butenyltin with phenylsulfenyl chloride [145]. The reaction mixture was irradiated in the Rayonet at 350 nm for 24 h.…”