2228-98-0

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 3033, 1986 DOI: 10.1021/ja00271a037

InChI:InChI=1/C10H18/c1-10(2,3)9-7-5-4-6-8-9/h4-5,9H,6-8H2,1-3H3

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 7453-05-6 toluene-4-sulfonic acid-(trans-4-tert-butyl-cyclohexyl ester) 
• 7453-04-5 cis-4-tert-butylcyclohexyl tosylate 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 23525-05-5 1-bromo-4-(tert-butyl)cyclohex-1-ene 
• 16963-28-3 4-t-butyl-1-(morpholin-4-yl)cyclohex-1-ene 
• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 77242-43-4 4-(tert-butyl)cyclohexyl 4-methylbenzenesulfonate 
• 253185-03-4 tert-butylbenzene 
• 74-89-5 methylamine 
• 75-09-2 dichloromethane 
• 937-05-3 cis-4-tert-butyl-1-cyclohexanol 
• 7789-69-7 phosphorus pentabromide 
• 110-83-8 cyclohexene 

Downstream Products

• 62444-44-4 r-4-tert-Butyl-c-1,t-2-bis(thiocyanato)cyclohexan 
• 17177-75-2 methyl ester of trans-4-tert-butylcyclohexanecarboxylic acid 
• 17177-76-3 methyl esters of cis-4-tert-butylcyclohexanecarboxylic acid 
• 129840-68-2 cis-(5-t-butyl-2-cyclohexenyl)trimethylsilane 
• 129840-68-2 trans-(5-t-butyl-2-cyclohexenyl)trimethylsilane 
• 80683-92-7 4-tert-butyl-2-phenylselenocyclohexanone 
• 80684-34-0 5-tert-Butyl-2-phenylselanyl-cyclohexanone 
• 15763-62-9 trans-4-(tert-butyl)cyclohexane-1-carbaldehyde 
• 15763-61-8 t-butyl-4 cyclohexanecarboxaldehyde cis 
• 74741-13-2 c-4-t-butyl-t-2-thiocyanatocyclohexan-r-1-ol 
• 74741-14-3 (1S,2S)-5-tert-Butyl-2-thiocyanato-cyclohexanol 

Relevant academic research and scientific papers

Aqueous Microdroplets Capture Elusive Carbocations

Carbocations are short-lived reactive intermediates in many organic and biological reactions that are difficult to observe. This field sprung to life with the discovery by Olah that a superacidic solution allowed the successful capture and nuclear magnetic resonance characterization of transient carbocations. We report here that water microdroplets can directly capture the fleeting carbocation from a reaction aliquot followed by its desorption to the gas phase for mass spectrometric detection. This was accomplished by employing desorption electrospray ionization mass spectrometry to detect a variety of short-lived carbocations (average lifetime ranges from nanoseconds to picoseconds) obtained from different reactions (e.g., elimination, substitution, and oxidation). Solvent-dependent studies revealed that aqueous microdroplets outperform organic microdroplets in the capture of carbocations. We provide a mechanistic insight demonstrating the survival of the reactive carbocation in a positively charged aqueous microdroplet and its subsequent ejection to the gas phase for mass spectrometric analysis.

Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis by N, N, N′, N″, N″-Pentamethyldiethylenetriamine

Sodium diisopropylamide (NaDA) in N,N-dimethylethylamine (DMEA) and DMEA-hydrocarbon mixtures with added N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDTA) reacts with alkyl halides, epoxides, hydrazones, arenes, alkenes, and allyl ethers. Comparisons of PMDTA with N,N,N′,N′-tetramethylethylenediamine (TMEDA) accompanied by detailed rate and computational studies reveal the importance of the trifunctionality and κ2-κ3 hemilability. Rate studies show exclusively monomer-based reactions of 2-bromooctane, cyclooctene oxide, and dimethylresorcinol. Catalysis with 10 mol % PMDTA shows up to >30-fold accelerations (kcat > 300) with no evidence of inhibition over 10 turnovers. Solid-liquid phase-transfer catalysis (SLPTC) is explored as a means to optimize the catalysis as well as explore the merits of heterogeneous reaction conditions.

A mild method for the replacement of a hydroxyl group by halogen: 2. unified procedure and stereochemical studies

N,N-Dimethyl- and N,N-diisopropyl-1-halo-2-methyl-l-propenylamines are readily available reagents for the mild deoxyhalogenation of alcohols and hydroxyacids. In this study we showed that the reactivity of the reagents can be tuned by varying the size of the alkyl groups on the reagents: the replacement of methyl by isopropyl groups led to a significant increase of reactivity. We then described a unified procedure for all deoxyhalogenations using the readily available α-chloroenamines as reagents with (bromination, iodination) or without (chlorination) an alkaline bromide or iodide. Finally, we showed that deoxyhalogenation reactions of secondary alcohols were highly stereospecific and generally occurred with inversion of configuration.

Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3coupling of carboxylic acids and π-electrophiles

A dual catalytic decarboxylative allylation and benzylation method for the construction of new C(sp3)-C(sp3) bonds between readily available carboxylic acids and functionally diverse carbonate electrophiles has been developed. The new process is mild, operationally simple, and has greatly improved upon the efficiency and generality of previous methodology. In addition, new insights into the reaction mechanism have been realized and provide further understanding of the harnessed reactivity.

Selectivity and Mechanism of Iridium-Catalyzed Cyclohexyl Methyl Ether Cleavage

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Introduction of Cyclopropyl and Cyclobutyl Ring on Alkyl Iodides through Cobalt-Catalyzed Cross-Coupling

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Sodium Diisopropylamide in N,N-Dimethylethylamine: Reactivity, Selectivity, and Synthetic Utility

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Tetramethylfluoroformamidinium hexafluorophosphate (TFFH) as a mild deoxofluorination reagent

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Efficient oxidation of 1,2-diols into a-hydroxyketones catalyzed by organotin compounds

Electrochemical oxidation of 1,2-diols with a catalytic amount of an organotin compound and a bromide ion as mediators has been developed. Various cyclic and acyclic 1,2-diols were oxidized into the corresponding α-hydroxyketones in good to excellent yields without C-C bond cleavage. Also, oxidation with the use of chemical oxidants was accomplished in the presence of a catalytic amount of an organotin compound. These reactions could discriminate 1,2-diols from isolated hydoxyl groups or 1,3-diols. In the case of a conformationally restricted cyclic 1,2-diol, the axial hydroxyl group was oxidized exclusively. Mono-, di-, and trialkylated tin compounds were examined as mediators and dialkylated tin compounds showed higher catalytic activity than mono- and trisubstituted ones. Me2SnCl2 was found to be the most suitable mediator for the selective oxidation..