74472-73-4Relevant academic research and scientific papers
Studies on the reactive species in fluoride-mediated carbon-carbon bond-forming reactions: Carbanion formation by desilylation with fluoride and enolates
Biddle, Margaret M.,Reich, Hans J.
, p. 4031 - 4039 (2007/10/03)
The reactive species in fluoride-mediated carbon-carbon bond-forming reactions was investigated. The regio- and diastereoselectivities of silanes reacting with cyclohexenone in the presence of a catalytic amount of fluoride was compared to the reactivity of analogous solvent-separated lithium ion pairs. Closely analogous behavior was observed, showing that carbanions and not siliconate complexes are the reactive species in the fluoride-catalyzed reactions. Spectroscopic investigations unambiguously show that phenylthiobenzyl anion will form by reaction of silane with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) or crypt[2.1.1]-solvated lithium enolates. The catalytic cycle runs smoothly with the crypt[2.1.1] complex of α-(phenylthio)benzyllithium as the initiator and enolate as the carrier of the desilylation reaction.
Selenium-Stabilized Carbanions. Acidity of Allyl and Vinyl Sulfides and Selenides
Reich, Hans J.,Willis, William W.
, p. 5227 - 5229 (2007/10/02)
The rates of deprotonation of vinyl and allyl aryl sulfides with amide bases show that allyl sulfides are kinetically more acidic than allyl selenides, whereas vinyl sulfides are less acidic than vinyl selenides.
