Alkyl bisulfates

The side reaction depicted in Equation 10.9 is avoided when the formation of the substitution product is reversible. For this reason, sulfuric acid is often used to effect the dehydration of alcohols in the imdergraduate laboratory because the intermediate alkyl bisulfate (Nu = HSO3O ) substitution product readily reionizes to the intermediate carbocation under the reaction conditions (Eq. 10.10). Subsequent loss of a proton then gives the desired alkene. 

Alkyl nitrates 509 react with chlorosulfonic acid at 15-20 °C to give excellent yields (90-94%) of the corresponding alkyl bisulfates 510 (Equation IbO)." This reaction provides a useful synthesis of alkyl bisulfates. 

Alkenes react with cold, concentrated sulfuric acid to form compounds of the general formula ROSO3H, known as alkyl hydrogen sulfates. These products are formed by addition of hydrogen ion to one side of the double bond and bisulfate... 

Diaryliodonium salts. This is a powerful electrophile to effect a Friedel-Crafts-type reaction of aromatic compounds (alkyl and haloarenes). Nitrobenzene reacts to give bis(m-nitrophenyl) iodonium bisulfate in 60% yield. 

In the synthesis of 2-alkylthio-3-quinazolin-4-ones 76 reported by Powers, treatment of isatoic anhydride (74), derived from anthranilic acid, with aminoacetonitrile followed by reaction with thiophosgene provided the quinazolinone 75 <01JHC419>. Alkylation of 75 led to the thioethers 76 in good to excellent yields. A very similar compound, quinazolin-2.4-dione 78, was synthesized from 77 and aminoacetonitrile bisulfate <01JOC4723>. 

See Dihydroxyethyl cocamine oxide Ethanol, 2,2 -iminobis-, sulfate (1 1) (salt). See Diethanolamine bisulfate Ethanol, 2,2 -iminobis-, N-tallow alkyl derivs.. See N-Tallow alkyl-2,2 -iminobisethanol Ethanol, 2,2 -iminobis-, N-tallow alkyl derivs., N-oxides. See Dihydroxyethyl tallowamine oxide Ethanol, 2-isobutyoxy-. See Ethylene glycol isobutyl ether... 

Iminobis (acetic acid). See Iminodiacetic acid 2,2 -lminobisethanol. See Diethanolamine 2,2 -lminobis (ethanol) sulfate 2,2 -Iminobisethanol sulfate (1 1) (salt). See Diethanolamine bisulfate 2,2 -lminobisethanol, N-tallow alkyl, N-oxide. See Dihydroxyethyl tallowamine oxide 2,2 -lminobisethylamine. See Diethylenetriamine... 

Eucalyptol PEG-4M Sodium alkyl sulfate Sodium bisulfate acetone dentifrices... 

The dichromate oxidation of tertiary alkyl aryl amines in a sulfate-bisulfate buffer was found to give secondary amines in good yields. Trialkylamines did not react under the conditions used,... 

Alkyl distribution gradient from 80 20 to 95 5 methanolic 0.5% tetrabutylammonium bisulfate/H20 in 30 min 2-phenyl content gradient 85 15 to 95 5 methanolic 0.5% hexa-decyltrimethylammonium bromide/H20 in 30 min unsulfonated material 94 6 MeOH/ H2O, back-flush after 4.5 min Gradient CH3CN/H20,0.02 M NaC104... 

Petroleum sulfonates, apparent total alkyl chain length C3-C28 determination of approximate alkyl Alltech RSIL prep C s precolumn, 4.6 X 32 mm, and Dupont Zorbax 10 C column, 4.6 x 250 mm Ternary gradient, tetrabutylammonium bisulfate, 0.1 M in H2O/H2O/CH3CN, pH 5 UV, 225 or 195 nm 35... 

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