154659-33-3Relevant academic research and scientific papers
Amphiphilic organocatalyst for schotten-baumann-type tosylation of alcohols under organic solvent free condition
Asano, Keisuke,Matsubara, Seijiro
supporting information; experimental part, p. 1757 - 1759 (2009/09/06)
A Tosylation of primary alcohol with tosyl chloride was performed effectively with an W-hexadecylimidazole catalyst in water containing K 2CO3 aggregation of the catalyst carrying a hydrophobic methylene chain worked as a substitute for organic solvent.
Aza cope rearrangement of propargyl enammonium cations catalyzed by a self-assembled "nanozyme"
Hastings, Courtney J.,Fiedler, Dorothea,Bergman, Robert G.,Raymond, Kenneth N.
supporting information; experimental part, p. 10977 - 10983 (2009/02/05)
The tetrahedral assembly [Ga4L6]12- [L = N,N-bis(2,3-dihydroxybenzoyl)-1,5-diaminonaphthalene) encapsulates a variety of cations, including propargyl enammonium cations capable of undergoing the aza Cope rearrangement. For propargyl enammonium substrates that are encapsulated in the [Ga4L6]12- assembly, rate accelerations by factors of up to 184 compared with the background reaction rate were observed. After rearrangement, the product iminium ion is released into solution and hydrolyzed, allowing for catalytic turnover. The activation parameters for the catalyzed and uncatalyzed reaction were determined, revealing that a decrease in the entropy of activation is responsible for the observed rate enhancements. The catalyzed reaction exhibits saturation kinetics: the rate data obeyed the Michaelis-Menten model of enzyme kinetics, and competitive inhibition using a nonreactive guest was demonstrated.
Nematic tolanes and acetylenes
Skelton, Graham W.,Dong, Dewen,Tuffin, Rachel P.,Kelly, Stephen M.
, p. 450 - 457 (2007/10/03)
The first liquid crystals incorporating a non-conjugated carbon-carbon triple bond in the terminal chain to exhibit a nematic phase above the melting point are reported. A variety of compounds incorporating a carbon-carbon triple bond in the terminal chain or between two phenyl rings have been synthesised as part of an investigation of the effects of the shape, conformation and rigidity of the terminal chains of liquid crystals on their mesophase behaviour. A series of related tolanes incorporating an alkenyloxy chain with an additional carbon-carbon double bond or a simple alkoxy chain as a terminal substituent also were prepared for comparison purposes.
Practical and efficient methods for sulfonylation of alcohols using Ts(Ms)Cl/Et3N and catalytic Me3N · HCl as combined base: Promising alternative to traditional pyridine
Yoshida, Yoshihiro,Sakakura, Yoshiko,Aso, Naoya,Okada, Shin,Tanabe, Yoo
, p. 2183 - 2192 (2007/10/03)
Several alcohols were smoothly and practically tosylated by two methods A and B. Method A uses the TsCl/Et3N (1.5 - 2.5 equiv)/cat. Me3N · HCl (0.1 - 1.0 equiv) reagent. Compared with the traditional Py-solvent method, the method A has merits of its much higher reaction rate, operational simplicity, economy in the use of the amine, and circumvention of the undesirable side reaction from R-OTs to R-CL. Method B uses TsCl/KOH [or Ca(OH)2]/cat. Et3N (0.1 equiv)/cat. Me3N · HCl (0.1 equiv) as the reagent, which will be suited for practical and large scale production for primary alcohols. On both methods A and B, a clear joint action of Et3N and Me3N · HCl catalysts was observed. 1H NMR measurements support the proposed mechanism of the catalytic cycle. Related methanesulfonylation using Et3N and cat. Me3N · HCl in toluene solvent also successfully proceeded, wherein the clear joint action was also observed.
