25246-83-7Relevant articles and documents
Skeletal Rearrangement for Water Loss from Molecular Protonated Ions of t-Butoxycyclohexane
Diakiw, Vladimir,Gordon, Patrick M.,Kingston, Eric E.,Shannon, James S.,Lacey, Michael J.
, p. 615 - 619 (1989)
Isotopic labelling and chemical substitution support the proposition that the skeletal rearrangement for water loss from molecular protonated ions of t-butoxycyclohexane involves competition between three reaction pathways.The principal reaction pathway (83percent) involves migration of the t-butyl group to the 2-(6-) position of the cyclohexyl ring with reciprocal hydrogen transfer.A second reaction pathway (12percent) involves ring contraction followed by reciprocal exchange of the t-butyl group with the 2-(5-) hydrogen atom of the nascent cyclopentyl ring.The third reaction pathway (5percent) involves rearrangement of a proton-bound complex to permit ipso attack by isobutene.Stereospecific substitutions indicate that the principal reaction pathway is susceptible to 1,3-diaxial interactions.
Zeolites Catalyze the Nazarov Reaction and the tert -Butylation of Alcohols by Stabilization of Carboxonium Intermediates
Blake, Finn,Leyva-Pérez, Antonio,Sanz-Navarro, Sergio,Tejeda-Serrano, María
, p. 2031 - 2037 (2020)
Zeolites are the most used catalysts worldwide in petrochemistry processes, with particular ability to stabilize carbocations. However, the use of zeolites in organic synthesis is still scarce. We show here that representative carboxonium-mediated organic
METHOD FOR PRODUCING ASYMMETRIC ALKYL ETHER HAVING TERTIARY ALKYL GROUP
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Paragraph 0028, (2017/01/31)
PROBLEM TO BE SOLVED: To provide a method capable of obtaining an asymmetric alkyl ether having a tertiary alkyl group easily and industrially. SOLUTION: (1) There is provided a method for producing an asymmetric alkyl ether having a tertiary alkyl group by subjecting a tertiary alcohol and a primary alcohol or a secondary alcohol to a dehydration reaction using activated clay as a catalyst. (2) There is provided the method for producing an asymmetric alkyl ether having a tertiary alkyl group according to (1), where the tertiary alcohol is any one selected from the group consisting of tert-butanol, tert-amylalcohol and 1-adamantyl alcohol. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
Gold(I)-catalyzed synthesis of unsymmetrical ethers using alcohols as alkylating reagents
Liu, Yongxiang,Wang, Xiaoyu,Wang, Yanshi,Du, Chuan,Shi, Hui,Jin, Shengfei,Jiang, Chongguo,Xiao, Jianyong,Cheng, Maosheng
, p. 1029 - 1036 (2015/03/30)
A microwave-irradiated alcohol-protecting strategy based on gold catalysis utilizing benzyl alcohol, tert-butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen-18 isotope labelled alcohols assisted by GC-MS techniques and chemical kinetic experiments. This strategy provides an efficient, straightforward and alternative approach to the preparation of benzyl, tert-butyl and trityl ethers in organic synthesis.
CATALYTIC C-H BOND ACTIVATION FOR THE SYNTHESIS OF ETHERS AND THIOETHERS
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Page/Page column 54-59, (2014/01/08)
Disclosed is a method for the transition metal-mediated oxidation of C-H bonds to form C-0 or C-S bonds. The methods are useful for the formation of ethers (R-OR') from alcohols, R'OH, and sp3 -hybridized C-H bonds in substrates, R-H. Aryl or heteroaryl acetates may also be used for C-H to C-OAr bond formation. The methods are also useful in the preparation of C-S bonds from acetyl-protected thiols, MeC(0)SR, and disulfides, RSSR. Advantageously, the methods minimize reaction steps, the handling of oxidized intermediates, and environmental impact.
An efficient synthesis of tert-butyl ethers/esters of alcohols/amino acids using methyl tert-butyl ether
Mallesha,Prahlada Rao,Suhas,Channe Gowda
experimental part, p. 641 - 645 (2012/02/15)
A facile synthesis of a wide variety of tert-butyl ethers and tert-butyl ester derivatives under mild conditions is described. Alcohols etherified with tert-butyl methyl ether as tert-butyl source and solvent, in the presence of sulfuric acid. Many amino acid tert-butyl esters have been synthesized by this procedure. The reaction is simple, inexpensive, easily scaled up, and proceeds without observable racemization. A green method was developed for the deprotection of this group using Amberlite resin IR 120-H as catalyst.
An eco-sustainable erbium(III) triflate catalyzed formation and cleavage of tert -butyl ethers
Procopio, Antonio,Costanzo, Paola,Curini, Massimo,Nardi, Monica,Oliverio, Manuela,Paonessa, Rosina
experimental part, p. 73 - 78 (2011/03/19)
An eco-compatible method, which permits the formation or cleavage of tert-butyl ethers of alcohols and phenols, is proposed. The protection step is performed in solvent-free conditions at room temperature using catalytic amount of Er(OTf)3. The catalyst is easily- recovered from the aqueous phase and reused several times without significant loss of activity. The deprotection step developed is also highly eco-friendly since the tert-butyl group is removed very quickly from alcohols and phenols in methanol using MW irradiation-. Georg Thieme Verlag Stuttgart · New York.
Saccharin sulfonic acid catalyzed N-Boc protection of amines and formation of tertbutyl ethers from alcohols
Shirini,Zolfigol,AbediniM.
experimental part, p. 603 - 607 (2010/10/21)
Saccharin sulfonic acid (SaSA), as a stable reagent is easily prepared by the reaction of saccharin with neat chlorosulfonic acid at room temperature. This compound is able to catalyze conversion of amines to their corresponding N-Boc protected amines with (Boc)2O. Alcohols were also converted to their corresponding tert-butyl ethers. All reactions took place under mild conditions giving the desired products in good to high yields.
A new, practical and efficient method for protecting alcohols as tert-butyl ethers
Barge, Alessandro,Occhiato, Ernesto G.,Prandi, Cristina,Scarpi, Dina,Tabasso, Silvia,Venturello, Paolo
experimental part, p. 812 - 816 (2010/06/14)
A new method for protecting alcohols as tert-butyl ethers is reported. The reaction is performed in tert-butyl acetate in the presence of a catalytic amount of HClO4. The process is extremely efficient and primary and secondary alcohols as well as diols are protected under very mild conditions. Remarkably, tert-butyl acetate can be easily recovered after the workup of the reaction and recycled.
Syntheses and conformational analyses of mono- and trans-1,4-dialkoxy substituted cyclohexanes-the steric substituent/skeleton interactions
Kleinpeter, Erich,Thielemann, J?rg
, p. 9071 - 9081 (2008/02/09)
Mono- and trans-1,4-dialkoxy substituted cyclohexanes (alkyl=Me, Et, i-Pr, t-Bu) were prepared using the solvomercuration-demercuration (SM-DM) procedure. The axial?axial and axial,axial?equatorial, equatorial conformational equilibria of the products wer
