1-Dodecyl tosylate

REDUCTION OF ALKYL HALIDES AND TOSYLATES WITH SODIUM CYANOBOROHYDRIDE IN HEXAMETHYL-PHOSPHORAMIDE (HMPA) A. 1-IODODECANE TO n—DECANE B. 1-DODECYL TOSYLATE TO n-DODECANE, 53, 107 REDUCTION OF KETONES BY USE OF TOSYLHYDRAZONE DERIVATIVES ANDROSTAN-17 0—OL, 52, 122 REDUCTIVE AMINATION WITH SO-... 

TBAF has been modified structurally around the anion to reduce its hygroscopic property. Several such reagents have been reported and their reaction with organic halides and sulfonate esters have been described. Tetrabutylammonium difluoride is ascribed to be a stable reagent and easily displaces halides and sulfonate esters.215 1-Dodecyl tosylate (18) is thus converted into 1-fluorododecane (19) in 96% yield. 

B. Reduction of 1-Dodecyl Tosylate to n-Dodecane. In a dry 200-ml. three-necked flask equipped exactly as described in Section A are placed 50 ml. of hexamethylphosphoramide (HMPA), 1-dodecyl tosylate (6.80 g., 0.0201 mole) (Note 8), and sodium cyanoborohydride (5.02 g., 0.080 mole) (Note 3). The solution is stirred at 80° for 12 hours (Note 9), then diluted with 50 ml. of water, and extracted with three 60-ml. portions of hexane. The hexane solution is washed twice with water, dried over anhydrous magnesium sulfate, and then concentrated at reduced pressure with a rotary evaporator. Distillation of the residue through a short-path apparatus (Note 5) (Cautionl foaming) affords 2.49-2.64 g. (73-78%) of w-dodecane, b.p. 79-81° (3.75 mm.) na4D 1.4217 (lit.,3 n20d 1.4219) (Note 7). 

NaBHjClSP 1-Iodododecane, HMPA, 25°C, 4h 1-Dodecyl tosylate, HMPA, 70° C, 8h... 

Dodecyl tosylate was prepared from 1-dodecanol by the procedure of Marvel and Sekera.5 Crystallization from a dried (magnesium sulfate) solution in light petroleum ether afforded white needles, m.p. 27.5-28.5°. 

Unilamellar vesicles prepared from mixtures of cetyl trimethylammonium tosylate and sodium dodecyl benzene sulfonate 8-Al203 prepared in vesicles Morphologies and sizes of 8-Al203 formed in vesicles were investigated by TEM and X-ray diffraction measurements use of vesicles as nanoreactors for the precipitation of ceramic particles was examined 129... 

Figure 1. Processing of picomavirus. polyprotein by proteolytic enzymes. The numbers in brackets represent molecular weights in thousands. Insert Sodium dodecyl sulfate/ polyacrylamide gel electrophoresis of poliovirus polypeptides, labelled with 5% methionine in infected HeLa cells, a. Infected, labelled at 2.5 hours post infection, b. Labelled in presence of 0.5 niM iodoacetamide. c. Labelled in presence of 0.1 mM tosyl lysine chloromethyl ketone.

FIGURE 3 Graph showing the uptake of [ Hlthymidine in VA-13 fibroblast (cell seeding density = 15,000 cells/cm-) culture on polypyrrole thin films containing various dopants. PP, polypyrrole PSS, poly(styrene sulfonate) Cl, chloride TsO, tosylate DSS, dodecyl sulfate DBzS, dodecyl benzene sulfonate. The uptake of thymidine is an indicator of cell proliferation. (Data from Ref. 21.)... 

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