6669-14-3Relevant academic research and scientific papers
Practical preparation of diphenylmethyl ethers from 2-diphenylmethoxypyridine using catalytic iron(III) chloride
Tran, Van Hieu,La, Minh Thanh,Kim, Hee-Kwon
, p. 6221 - 6228 (2019/07/04)
A novel facile synthetic method for producing diphenylmethyl (DPM) ethers from 2-diphenylmethoxypyridine was developed. A variety of DPM ethers was successfully achieved with high yield via treatment of alcohols with 2-diphenylmethoxypyridine in the presence of catalytic FeCl3. The procedure is a practical and efficient synthetic procedure to protect various alcohols, and it can be applied to prepare bioactive compounds.
Protecting group-free use of alcohols as carbon electrophiles in atom efficient aluminium triflate-catalysed dehydrative nucleophilic displacement reactions
Cullen, Adam,Muller, Alfred J.,Williams, D. Bradley G.
, p. 42168 - 42171 (2017/09/11)
Benzylic and allylic alcohols are rendered electrophilic without chemical modification by the use of aluminium triflate as catalyst. The reaction succeeds with alcohol, thiol, carbon and nitrogen nucleophiles. When phenols are employed as nucleophiles, C-alkylation ensues. An advanced application of the method is demonstrated in the synthesis of 2H-chromenes and their N and S analogues.
Boron Trifluoride?Diethyl Ether-Catalyzed Etherification of Alcohols: A Metal-Free Pathway to Diphenylmethyl Ethers
Li, Jiaqiang,Zhang, Xiaohui,Shen, Hang,Liu, Qing,Pan, Jing,Hu, Wen,Xiong, Yan,Chen, Changguo
supporting information, p. 3115 - 3120 (2015/11/03)
A novel boron trifluoride?diethyl ether (BF3?OEt2)-catalyzed etherification procedure has been developed in which primary and secondary alcohols are easily converted into diphenylmethyl ethers with yields of up to 99%.
Iodine-catalyzed nucleophilic substitution reactions of benzylic alcohols
Srihari, Pabbaraja,Bhunia, Dinesh C.,Sreedhar, Pamu,Yadav, Jhillu S.
experimental part, p. 1045 - 1049 (2009/04/04)
Molecular iodine efficiently catalyzes the direct nucleophilic substitution of the hydroxy group of benzylic alcohols with carbon and oxygen nucleophiles. Georg Thieme Verlag Stuttgart.
Niobium(V) pentachloride: an efficient catalyst for C-, N-, O-, and S-nucleophilic substitution reactions of benzylic alcohols
Yadav,Bhunia, Dinesh C.,Vamshi Krishna,Srihari
, p. 8306 - 8310 (2008/03/30)
Benzylic alcohols undergo easy C-, N-, O-, and S- centered nucleophilic substitution reactions with a catalytic amount of NbCl5.
PdCl2, a useful catalyst for protection of alcohols as diphenylmethyl (DPM) ethers
Bikard, Yann,Weibel, Jean-Marc,Sirlin, Claude,Dupuis, Luc,Loeffler, Jean-Philippe,Pale, Patrick
, p. 8895 - 8899 (2008/03/14)
Primary, secondary, benzylic and allylic alcohols are efficiently converted to the corresponding diphenylmethyl ethers in the presence of catalytic amounts of PdCl2.
Nafion-catalyzed preparation of benzhydryl ethers
Stanescu, Marina A,Varma, Rajender S
, p. 7307 - 7309 (2007/10/03)
Nafion-H is found to be an efficient and recyclable catalyst for the preparation of diphenylmethyl ethers of alcohols.
Reactions of Carbenes with Oxetane and with Oxetane/ Methanol Mixtures
Kirmse, Wolfgang,Lelgemann, Rudolf,Friedrich, Klaus
, p. 1853 - 1863 (2007/10/02)
Ethoxycarbonylcarbene, bis(methoxycarbonyl)carbene, phenylcarbene (17a), diphenylcarbene (17b), fluorenylidene (17c), 2-furylcarbene (31a), 2-furyl(phenyl)carbene (31b), 4-oxo-2,5-cyclohexadienylidene (40), and 4,4-dimethyl-2,5-cyclohexadienylidene (53) were generated by photolysis of the appropriate diazo compounds.With neat oxetane, most of these carbenes react by competitive C-H insertion (B -> A, Scheme 1) and ylide formation (B -> C). 31a and 40 do not insert into C-H bonds; 31b does not attack oxetane but rearranges exclusively with formation of 26.The ylides undergo Stevens rearrangement to give tetrahydrofurans (C -> D) and α',β-elimination, leading to allyl ethers (C -> E).With oxetane/ methanol mixtures, the intervention of oxonium ions (H) is indicated by the formation of 1,3-dialkoxypropanes (I).The oxonium ions arise either by protonation of the ylides (C -> H) or by protonation of the carbenes (B -> G), followed by electrophilic attack of the carbocations (G) at oxetane (G -> H).The former route is followed by the alkoxycarbonylcarbenes and by 40; the ylides derived from the remaining carbenes do not react with methanol, owing to their rapid Stevens rearrangements.Protonation of the carbenes 17b, 31, and 53 is clearly indicated by their product ratios and, for 31, by the formation of isomeric ethers (33, 36).The more electrophilic carbenes discriminate but slightly between oxetane and methanol while the more nucleophilic carbenes (17b, 31, 53) prefer the protic methanol strongly over the aprotic oxetane. Key Words: Carbenes/ Oxygen ylides/ Stevens rearrangement/ Oxonium ions/ Insertion, O-H/ Ylides
