The reaction of some perhalosilanes with benzaldehyde

Webb, A.F.; Sethi, D. S.; Gilman, Henry

doi:10.1016/s0022-328x(00)83617-7

Cited by 24 publications

(3 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, Gostevskii et al used (perfluorophenyl)trimethylsilane to carry out the perfluorophenylation of aldehydes in the presence of cyanide ion under neutral conditions (eq 65). − Cesium fluoride can also be used as an initiator for this process. In the absence of an anionic initiator the addition proceeds only at 170 °C . Enolizable ketones lead to silyl enol ethers rather than to addition products under these conditions.…”

Section: 33 Perfluoroarylationmentioning

confidence: 98%

See 1 more Smart Citation

Perfluoroalkylation with Organosilicon Reagents

1997

View full text Add to dashboard Cite

in the Chemistry Department at USC in the tenure track. He was promoted to full professorship in 1994. Currently, he holds the Olah Nobel Laureate Chair in Hydrocarbon Chemistry with research contributions and interests in new fluorination methods, new synthetic methods, mechanistic studies of organic reactions, electrochemistry, and superacid and hydrocarbon chemistry. He has published more than 300 papers, book chapters, and review articles; coauthored 4 books; and holds 3 patents. He has received many honors and recognition. He is currently an Advisory Editor of the International Journal of Porphyrins and Pthalocyanins.

show abstract

Section: 33 Perfluoroarylationmentioning

confidence: 98%

“…In the absence of an anionic initiator the addition proceeds only at 170 °C. 107 Enolizable ketones lead to silyl enol ethers rather than to addition products under these conditions. This is attributed to the stabilizing effect of perfluorophenyl group on the evolving negative charge in the course of enolization.…”

Section: Perfluoroarylationmentioning

confidence: 99%

Perfluoroalkylation with Organosilicon Reagents

1997

View full text Add to dashboard Cite

show abstract

“…absence of KF the reaction requires a temperature of 170 °C. 28 Other nucleophiles, such as CN", in place of F" cause C6F5SiMe3 to react with ketones to produce silyl enol ethers resulting from abstraction of -hydrogen by C6-Fs".29"31 Metal fluoride-induced reactions of carbonyl compounds with other electronegatively-substituted aryltrimethylsilanes have also been investigated. 32 The general use of organosilicon compounds with nucleophilic catalysts has been reviewed.…”

Section: Introductionmentioning

confidence: 99%