85686-16-4Relevant 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.
Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions
Howard, Kyle T.,Duffy, Brian C.,Linaburg, Matthew R.,Chisholm, John D.
supporting information, p. 1623 - 1628 (2016/02/09)
Alcohols are effectively converted to their corresponding diphenylmethyl (DPM) ethers by reaction with O-diphenylmethyl trichloroacetimidate in refluxing toluene without the requirement of a catalyst or other additives. A number of acid and base sensitive substrates were protected in excellent yield using this new method without disturbing the pre-existing functionality present in these molecules. This reaction is the first example of the formation of an ether from stoichiometric amounts of a trichloroacetimidate and an alcohol without the addition of a Br?nsted or Lewis acid catalyst.
The Role of Single-Electron Transfer in SN2-Type Substitution Reactions of Anions with Alkyl Halides
Bordwell, F.G.,Harrelson, John A.
, p. 4893 - 4898 (2007/10/02)
Rate constants (kobsd) for reactions of electrophiles with: (a) various carbanions, including 9-substituted fluorenide ions (9-GFl-), 9-substituted xanthenide ions, α-cyano carbanions, anb β-diketo enolate ions, (b) phenothiazinide (PTZ-) and carbazole (Cb-) nitranions, (c) 4-substituted phenoxide ions, and (d) thiphenoxide ions, have been campared with rate constants for single-electron transfer (kSET) calculated using a Marcus-type equation.For both 9-GFl- carbanion and 2-GPTZ- nitranion families reacting with SET acceptors, such as 1,1-dinitrocyclohexane, the kobsd/kSET ratio is near unity.For 9-GFl- carbanions reacting with Ph2CHCl the kobsd/kSET ratios range from 2 to 105, those for 2-PTZ- nitranions from 370 to 1.3*104, and those for Cb- nitranions from 108 to 1010.For reactions of 4-GC6H4O- oxanions with Ph2CHCl the ratios range from 103 for G = Me2N to 1013 for G = CN; for PhS- ion reacting with n-BuBr the ratio is 1017.The significance of these results with respect to the role of an outer sphere SET mechanism in substitution reactions of anions with alkyl halides is discussed.
ACTIVATION BY PdCl2(PhCN)2 OF THE ALCOHOLIC BENZYLIC FUNCTION TO NUCLEOPHILIC ALIPHATIC AS WELL AS ELECTROPHILIC AROMATIC SUBSTITUTIONS. A ONE STEP SYNTHESIS OF A CHROMANE STRUCTURE
Mincione, Enrico,Bovicelli, Paolo
, p. 437 - 440 (2007/10/02)
Benzylic alcohols react, by activation with PdCl2(PhCN)2, under mild conditions with alkanols and enols to give the corresponding benzylic ethers, and, under the same conditions, with aromatic substrates to give the corresponding phenylmethanes.As an example, a one-step synthesis of a chromane structure is reported.
