4282-44-4Relevant articles and documents
Direct Trifluoromethoxylation without OCF3-Carrier through In Situ Generation of Fluorophosgene
Donnard, Morgan,Guérin, Thomas,Hanquet, Gilles,Leroux, Frédéric R.,Panossian, Armen,Saiter, Jérémy
supporting information, p. 3139 - 3147 (2021/06/26)
Owing to the high interest in the OCF3 group for pharmaceutical and agrochemical applications, trifluoromethoxylation received great attention in the last years with several new methods for this approach towards OCF3-comprising compounds. Yet, it most often requires the beforehand preparation of specific F3CO? transfer reagents, which can be toxic, expensive, unstable, and/or generate undesired side-products upon consumption. To circumvent this, the in-situ generation of gaseous fluorophosgene from triphosgene, its conversion by fluoride into the OCF3 anion, and the direct use of the latter in nucleophilic substitutions is an appealing strategy, which, although recently approached, has not been fully exploited. We disclose herein our efforts towards this aim.
Homogeneous catalysis, heterogeneous recycling: A new family of branched molecules with hydrocarbon or fluorocarbon chains for the Friedl?nder synthesis of quinoline under solvent-free conditions
Fang, Lei,Yu, Jianjun,Liu, Ying,Wang, Anyin,Wang, Limin
, p. 11004 - 11009 (2014/01/06)
A new family of branched catalysts with hydrocarbon or fluorocarbon chains was used to catalyze Friedl?nder reaction between 2-aminoarylketones and α-methylene ketones under solvent-free conditions in good to excellent yields. The catalysts exhibit temperature-dependent solubility and such a thermomorphic character allows them to be recovered by filtration conveniently at room temperature and reused at least five times. To some extent, the branched catalysts with hydrocarbon chains are superior to those with fluorocarbon chains, as they are cheaper and more biodegradable.
New halogenation reagent system for one-pot conversion of alcohols into iodides and azides
Kamal, Ahmed,Ramesh,Laxman
, p. 827 - 833 (2007/10/03)
In Situ generation of hydrogen iodide from methanesulphonic acid/sodium iodide in different solvents was found to be an attractive reagent system for the chemoselective conversion of various alcohols to their corresponding iodides. Moreover, treatment of benzylic and allylic alcohols with this reagent system, followed by substitution with azide ion, produced the corresponding azides in one pot in good yields.
Intramolecular homolytic displacements. 30. Functional decarbonylative transformations of aldehydes via homolytically induced decomposition of unsaturated peroxyacetals
Degueil-Castaing, Marie,Moutet, Laurent,Maillard, Bernard
, p. 3961 - 3965 (2007/10/03)
Homolytically induced decompositions of unsaturated peroxyacetals, synthesized from aldehydes, gave alkoxyalkoxyl radicals that yielded alkyl radicals by rapid β-scission. The latter radicals could react with several types of "transfer agents" to smoothly bring about homolytic decarbonylative functional group transformations of aldehydes into halides, hydrocarbons, xanthates, alkanenitriles, 2-alkyl-3-chloromaleic anhydrides, 1-phenylalk-1-ynes, and ethyl 2-alkylpropenoates.
Functional transformation of aldehydes and ketones via homolytic induced decomposition of unsaturated peroxy acetals and peroxy ketals
Moutet,Bonafoux,Degueil-Castaing,Maillard
, p. 139 - 140 (2007/10/03)
Induced decomposition of unsaturated peroxy acetals prepared from trimethyl orthoformate, dodecanal or 2-methyl-undecanal and 2,3-dimethyl-2-hydroperoxybut-3-ene, in the presence of ethyl iodoacetate, CC14 or dodecanethiol, allowed respectively their iodo-, chloro- and hydro-decarbonylation with yields of over 70%; the same reaction applied to the monoperoxy ketal or diperoxy ketal of cyclohexanone in the presence of ethyl iodoacetate resulted in its functional transformation in methyl 6-iodohexanoate or 1,5-diiodopentane with respective yields of 65 and 40%.
Enantioselective Synthesis of (R)-(+)-5-Hexadecanolide, the Pheromone of Queen of Oriental Hornet, Vespa orientalis Linn
Gadkari, R. G.,Kapadi, A. H.
, p. 814 - 815 (2007/10/02)
An enantioselective synthesis of (R)-(+)-5-hexadecanolide (1) using cyclopentanone, and (R)-2-aminobutyl-n-undecyl iodide (as electrophile) is reported.
Synthetic Methods and Reactions. 112. Synthetic Transformations with Trichloromethylsilane/Sodium Iodide Reagent
Olah, George A.,Husain, Altaf,Singh, Brij P.,Mehrotra, Ashok K.
, p. 3667 - 3672 (2007/10/02)
A new, convenient, and inexpensive alternative to the in situ equivalent of iodotrimethylsilane was developed.A mixture of trichloromethylsilane/sodium iodide in dry acetonitrile is found to be a more selective reagent than chlorotrimethylsilane/sodium iodide for the cleavage of ethers, esters, and lactones.Ethers are cleaved regioselectively by this reagent.Cleavage of esters and lactones also occured more readily with the present system.Conversion of alcohols, particularly tertiary and benzylic alcohols, to corresponding iodides is achieved in very short times at ambient temperatures.Deoxygenation of sulfoxides to sulfides is found to be instantaneous.Reductive dehalogenation of alicyclic α-halo ketones to the corresponding ketones has also been studied.The reagent is also used for the deprotection of acetals to carbonyl compounds.
PREPARATION OF ALKYL HALIDES VIA ORGANOTELLURIUMS
Chikamatsu, Kiyofumi,Otsubo, Tetsuo,Ogura, Fumio,Yamaguchi, Hachiro
, p. 1081 - 1084 (2007/10/02)
The conversion of phenyltelluroalkanes to haloalkanes was studied in connection with the homologation of alkyl halides.Similar reactions of 1,1-bis(phenyltelluro)alkanes provided a new synthetic method of aldehydes.
