34694-32-1Relevant articles and documents
Gem-Heterosubstituted (stannyl)methylsilanes as synthetic equivalents of functionalized α-stannyl(methyl) anions
Tanini, Damiano,Nocentini, Tiziano,Capperucci, Antonella
, p. 99 - 113 (2020/02/13)
α-Heterosubstituted silyl derivatives, such as phenylthio-, phenylseleno- and benzotriazolyl-stannyl silanes, react with aldehydes under tetra-n-butylammonium fluoride (TBAF) catalysis, leading to α-substituted-βhydroxy stannanes, able to behave as precursors of Z- and E-olefins, generated by deoxystannylation. This reactivity shows the capability of such heterosubstituted silanes to act as masked carbanions through a mild functionalization of the carbon-silicon bond.
Silyl-substituted dithioles as candidates for new electron donors
Li,Nishiwaki,Itami,Yoshida
, p. 1717 - 1725 (2007/10/03)
Molecular orbital calculations revealed that the introduction of a silyl group onto the 2-position of 1,3-dithiole caused significant decrease of the ionization potential and that 2-silyl-1,3-dithioles served as a pseudo π-electron system. The silyl group could also be utilized as a bridge for linking π-electron systems to achieve artificial stacking. These concepts led us to the design and synthesis of silyl-substituted 1,3-benzodithioles as candidates for new electron donors. The oxidation potential of monosilyl-substituted 1,3-benzodithiole was found to be significantly less positive than that of the parent 1,3-benzodithiole. The introduction of the second silyl group caused further decrease of the oxidation potential. Compounds composed of two 1,3-benzodithiole units linked by a silyl group were also synthesized. These showed comparable oxidation potentials to those of the corresponding monomeric compounds. The effect of stannyl-substitution onto the 2-position of 1,3-dithiole was found to be larger than that of silyl-substitution. The effects of silyl-1 and stannyl-substitution for related systems such as thioanisole and 1,3-dithiane were also studied.
