101417-70-3Relevant academic research and scientific papers
Nucleophilic perfluoroalkylation of aldehydes, ketones, imines, disulfides, and diselenides
Pooput, Chaya,Dolbier Jr., William R.,Medebielle, Maurice
, p. 3564 - 3568 (2006)
Using a procedure analogous to that developed for nucleophilic trifluoromethylation, the perfluoroalkyl anion reagents created by mixing C 2F5I and n-C4F9I with tetrakis(dimethylamino)ethylene (TDAE) were effective in their nucleophilic reactions with aldehydes, ketones, imines, disulfides, and diselenides. Irradiation proved beneficial in the aldehyde and ketone reactions.
Preparation of Trifluoromethyl and Other Perfluoroalkyl Compounds with (Perfluoroalkyl)trimethylsilanes
Krishnamurti, Ramesh,Bellew, Donald R.,Prakash, G. K. Surya
, p. 984 - 989 (2007/10/02)
The preparation of a variety of novel perfluoroalkyl-substituted compounds in high yields using easily prepared (perfluoroalkyl)trimethylsilanes (1a - c) is described. (Trifluoromethyl)-, (pentafluoroethyl)-, and (heptafluoropropyl)trimethylsilane, 1a - c, respectively, react readily with carbonyl compounds, such as aldehydes and ketones, by a fluoride-initiated catalytic process.Fluoride-initiated addition of 1 to a carbonyl group generates an oxyanionic species which then further catalyzes the reaction.Even enolizable carbonyl compounds react cleanly under the reaction conditions.A study of the scope of the reactivity of 1a toward other carbonyl groups in esters, lactones and an acid chloride was also carried out.Thus 1a reacts cleanly with five- and six-membered ring lactones.However, unactivated esters do not react under the reaction conditions.The acid chloride reacts with 1a to give a mixture of products.
Nucleophilic Addition of the Pentafluoroethyl Group to Aldehydes, Ketones, and Esters
Gassman, Paul G.,O'Reilly, Neil J.
, p. 2481 - 2490 (2007/10/02)
Pentafluoroethyl iodide reacts with methyllithium at -78 deg C to produce (pentafluoroethyl)lithium.This halogen-metal exchange reaction can be carried out in the presence of aldehydes, ketones, and esters with no observable addition of methyllithium to t
PENTAFLUOROETHYLLITHIUM. GENERATION AND USE IN SYNTHESIS
Gassman, Paul G.,O'Reilly, Neil J.
, p. 5243 - 5246 (2007/10/02)
Pentafluoroethyl iodide undergoes a rapid exchange reaction with methyllithium at -78 deg C in the presence of ketones to produce pentafluoroethyl-substituted tertiary carbinols in high yield.
