Cyclohexyl p toluenesulfonate

Reactions of Cyclopropyl, Cyclobutyl, Cyclopentyl and Cyclohexyl-p-Toluenesulfonates and Halides. J. Amer. chem. Soc. 73, 5034 (1951). 

In contrast, a secondary tosyloxy group attached to a carbon atom engaged in a 5- or 6-membered ring (see Tables V, VI, VII) is relatively unreactive. Thus, cyclohexyl p-toluenesulfonate, under the above... 

Cyclohexyl p-toluenesulfonate Cyclohexyl tosylate. See Cyclohexyl 4-toluenesulfonate 3-Cyclohexyl-5,6-trimethyleneuracil. See Lenacil... 

A variety of 2,5-dialkylfurans are available via the Paal-Knorr condensation cyclization is possible for both hindered and unhindered 1,4-diketones. Fleming prepared 2-cyclohexyl-5-methylfuran (31) in 91% yield via treatment of dione 30 with catalytic p-toluenesulfonic acid in refluxing benzene. Using the same methodology, Denisenko synthesized furan 33 in 35% yield from the corresponding dione (32). ... 

Calf thymus (CT) DNA was first fragmented by sonication, then purified by a standard procedure. Agarose gel electrophoresis for the sonicated CT DNA revealed a distribution in molecular weight ranging from 30 kDa to 260 kDa which is equivalent in base pairs (bp) from 40 to 400 (1 bp = 660 Da). The DNA fragments were reacted with HEDS in the presence of l-cyclohexyl-3-(2-morpholinoethyl) carbodi-imide metho-p-toluenesulfonate (CMC/jTs). Finally, the reaction mixture was gel-filtered and the macro-molecular fractions, when displayed the characteristic absorption of 260 nm of the nucleic bases, were collected. 

Namely, the reaction of 2-thioxothiazolidin-4-one N-hexanoic acid (116) with 2,5-dimethyl-l-phenylpyrrol-3-carboxaldehyde (117) in methanol under the catalytic action of ethylenediamine diacetate (EDDA) yields 5-[(2,5-dimethyl-l-phenylpyrrol-3-yl)methylidene]-2-thioxothiazolidin-4-one N-hexanoic acid (118) in 79% yield. The hydroxamate derivative of 118 is prepared by reacting this compound with 0-(tetrahydro-2H-pyran-2-yl)hydroxylamine followed by treatment with p-toluenesulfonic acid in methanol to afford compound 121 in 60% yield. Esterification of compound 118 is carried out by using methyl iodide in acetonitrile in the presence of sodium carbonate to give compound 120. The 5-(cyclohexyl)methylidene analogue (119) is obtained in 42% yield by direct reaction of compound 116 with cyclohexanecar-boxaldehyde in methanol under the catalytic action of EDDA. 

METHOD 2. A mixture of 170 g of piperidine, 220 g of cyclohexylamine, and 750 ml of benzene is azeotropically distilled until the evolution of H2O stops, then vacuum distill to get cyclohexenyl-piperidine. p-toluenesulfonic acid monohydrate (190 g) in 250 ml of PhMe is heated under a water trap until all the H2O is removed, then add a solution of 165 g of cyclohexyl-piperidine in 500 ml of Et20, with cooling, to keep temp at 0°. A solution of 1 mole of PlMgBr (made from 157 g of PhBr and 24 g of Mg) in 750 ml of Et20 is added (still holding the temp at 0° to 5°). The mixture is stirred for an additional 30 min... 

Moffatt et al.13 mentioned that other carbodiimides, such as diisopropylcarbodii-mide, can be used in place of DCC. Carbodiimides, other than DCC and EDC, occasionally employed in this oxidation include diethylcarbodiimide19 and 1 -cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate.20 It... 

Table 2.2. lists activators used less commonly for Moffatt oxidations. The following activators, namely diphosgene,262 triphosgene,263 2-chloro-1,3-dimethylimidazolinium chloride,264 l-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulfonate,265 triphenylphosphine dibromide and dichloride,266 and phenyl dichlorophosphate,267 have been the subject of scientific monographs, in which they are proposed as suitable and convenient alternatives to more routinely used activators, and can offer improved oxidation conditions in some substrates. 

OX AZOLINE-5 -ONES 1 Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate. 

The kinetics of the reaction of the water solnble N-cyclohexyl-N -(4-methylmorpholine-/3-yl) carbodiimide p-toluenesulfonate with carboxylic acid was also investigated." The... 

The racemic tetracyclic amine (3) can be coupled to ( )-(+)-p-tolylsulfinylacetic acid using the modified carbodi-imide reagent l-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide Metho-p-toluenesulfonate to give the diastereomeric sulfinyl amides (4) and (5) (eq 2), which are readily separated by HPLC. ... 

Abbreviations EDC, l-ethyl-3-(3-dimethylaminopropyl)carbodiimide DCC, N,N -dicyclohexylcarbodiimide CMC, I -cyclohexyl-3(2-morpholinylethyl)carbodiimide metho-p-toluenesulfonate... 

Alkyl fluorides by way of/7-toluenesulfonates 963 The /7-toluenesulfonate (1 mole) is heated, with stirring, with KF (5 moles) in diethylene glycol (b.p. 245°), usually under reduced pressure (20-500 mm) the alkyl fluoride, most of which is evolved in the first 2 h, is trapped in suitable cold receivers. The weight of diethylene glycol used is the same as that of the KF. Temperatures used are 70-240°, with reaction times of 3-9 h. Cyclohexyl /7-toluenesulfonate gives cyclohexene phenyl /7-toluenesulfonate does not react. 

Pfitzner-Moffatt oxidation (1, 304-307 2, 162 3, 121). Improved results have been obtained by substitution of DCC with the water-soluble diimide 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulfonate (.see 1, 181 supplier Aldrich).. ... 

Fig. 5. Plot of actual ( ) and calculated values (solid line) of acetolysis (25°C) rate constants versus calculated substituent constants for cyclic and polycyclic secondary alkyl p-toluenesulfonates. The solid line is defined by actual acyclic secondary acetolysis results and is for substrates. The solid circles are 1, cyclopentyl 2, cyclohexyl 3, cycloheptyl 4, cyclo-tridecyl 5, cyclopentadecyl 6, cycloheptadecyl 7, 7-norbornyl 8,2-adamantyl 9,7,7-dimethyl-e do-2-norbornyl 10, a f/-7-norbornenyl 11, 7-norbornadienyl 12, gxo-2-benzonorbornenyl 13, exo-2-norbornyl 14, endo-l-norbornyl 15, 7,7-dimethyl-exo-2-norbornyl 16, 1-methyl-exo-2-norbornyl 17, 6,6-dimethyl-gni/o-2-norbornyl 18, l-methyl-gni/o-2-norbornyl 19, cyclobutyl.

Two of the most commonly used sulfonyl chlorides are p-toluenesulfonyl chloride (abbreviated tosyl chloride, TsCl) and methanesulfonyl chloride (abbreviated mesyl chloride, MsCl). Treating ethanol with p-toluenesulfonyl chloride in the presence of pyridine gives ethyl p-toluenesulfonate (ethyl tosylate). Pyridine is added to catalyze the reaction and to neutralize the HCl formed as a by-producf. Cyclohexanol is converted to cyclohexyl methanesulfonate (cyclohexyl mesylate) by a similar reaction of cyclohexanol with methanesulfonyl chloride. 

Benzene, iV AT-dimethylfcnmamide (DMF), dichlorometiiane, metiiyl methacrylate, tert-butyl methacrylate (TBMA) and p-terT-butoxystyrene (tBOSt) were purchased and distilled before use. 2,2 -Azobisisobutyronitrile (AIBN) was purified by recrystallization from etiianol. 9-Fluorenilideneimino p-toluenesulfonate (FITS) (72), neopentyl styrenesulfonate (NPSS) (73), cyclohexyl styrenesulfonate (CHSS) (14) and phenyl styrenesulfonate (PhSS) were prepared according to the lito ture. Qxone (potassium... 

Preparation of DNA-lmmobilized Electrode. DNA double strands were immobilized on a Au electrode via chemisorption, /.e., a co-ordination to Au with a sulfur-containing moiety (70). Sonicated calf thymus DNA (30-230 bp, 10 mg) was reacted with 2-hydroxyethyl disulfide (HEDS, 4.6 mg) in the presence of 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate (Aldrich, 0.4 g) in 0.4 cm of 0.04 M MES buffer (pH 6.0) for 24 h at 25 to give a phosphodiester linkage between the terminal monophosphate ends of the DNA and the hydroxyl group of HEDS (77). The reaction mixture was gel-filtrated on an NAP-10 column (Pharmacia), and the macromolecular fractions which displayed the characteristic absorption at 260 nm of the nucleic bases were collected. In the combined fractions containing the disulfide-modified DNA (0.3 mM in base-pair concentration), a polished Au disk electrode (1.6 mm diameter, Bioanalytical Systems) was inunersed for 24 h at 5 The modified electrode was then washed with and stored in TE buffer (10 mM Tris-HCl, 1 mM EDTA pH 7.2) at 5 XI before and between uses. 

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