17745-52-7Relevant academic research and scientific papers
Nucleophilic trifluoromethylation of carbonyl compounds and disulfides with trifluoromethane and silicon-containing bases
Large,Roques,Langlois
, p. 8848 - 8856 (2007/10/03)
Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)2N- M+, generated in situ from N(TMS)3 and M+ F- or RO- Na+. When F- is used in a catalytic amount, silylated α-(trifluoromethyl)carbinols are obtained: In this case, the four-component system HCF3/N(TMS)3/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)3/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of awl disulfides whereas N(SiMe3)3/F- is Well suited to that of aliphatic disulfides.
TOTAL SYNTHESIS OF (-)-PERIPLANONE-B, NATURAL MAJOR SEX-EXCITANT PHEROMONE OF THE AMERICAN COCKROACH, PERIPLANETA AMERICANA
Kitahara, Takeshi,Mori, Masataka,Mori, Kenji
, p. 2689 - 2700 (2007/10/02)
The total synthesis of (-)-periplanone-B 1, the major sex excitant and attractant pheromone of the American cockroach was accomplished starting from (+)-dihydrolimonene 2.Intramolecular alkylation of the substituted α-phenylthioacrylate 10 gave rise to the (E)-cyclodecene 11.Second key reaction was the reductive elimination of vicinal phenylthiobenzoate 14 to provide the cojugated diene 15.Overall yield of 1 through 28 steps was 0.5 percent.
A New Synthetic Method for Sulphenimines. Fluoride-catalysed Reaction of N,N-Bis(trimethylsilyl)sulphenamides with Aldehydes and Ketones
Morimoto, Toshiaki,Nezu, Yoshitaka,Achiwa, Kazuo,Sekiya, Minoru
, p. 1584 - 1585 (2007/10/02)
A convenient, general method for the preparation of sulphenimines by the reaction of aldehydes and ketones with N,N-bis(trimethylsilyl)sulphenamides in the presence of tetrabutylammonium fluoride catalyst is described.
