Sulfone alkylation

Because halides are poorer leaving groups than p toluene sulfonate alkyl p toluene sulfonates can be converted to alkyl halides by 8 2 reactions involving chloride bro mide or iodide as the nucleophile... 

Between sulfur dioxide radical anions, dithionite, and sulfoxylate/sulfite there exists a pH-dependent equilibrium465 (equation 86). Therefore, dithionite has been used as a source of sulfoxylate in order to prepare sulfinate and hence sulfones. Alkylation with triethyl oxonium fluoroborate leads to ethyl ethanesulfinate, alkyl iodides lead to symmetrical sulfones466 (equation 87). 

Treatment of a-sulfonyl carbanion with (iodomethyl)trimethylsilane gave / -trimethylsilyl sulfones " . Alkylation of jJ-trimethylsilyl sulfones 235 gave various -trimethylsilyl sulfones . The use of (iodomethyl)tributylstannane instead of (iodomethyl)trimethylsilane was shown to afford a tributylstannanyl derivative . This compound has been used for syntheses of terminal olefins " . 

Surfactants Alkyl benzene sulfonates, alkyl sulfates... 

Nozaki reported the reaction of trialkylboranes with styryl sulfoxides and sulfones. Alkyl radicals generated from trialkylboranes add at the -position of /3-styryl sulfoxides and sulfones (a- to the sulfur atom). The resulting radicals fragment and deliver the -styryl adducts [108]. Interestingly, the sulfoxides eliminate very rapidly leading to partially stereospecific substitution (Scheme 44). The radical nature of the process is demonstrated by the presence of a side product derived from the solvent (THF) by hydrogen atom abstraction. 

Scheme 7 Stepwise construction of the macrocycle, part I sulfone alkylation...

Scheme 9 Intramolecular sulfone alkylation and oxidative transposition...

Scheme 12 Functional and protecting group transformations and a sulfone alkylation for chain elongation...

Alkyl hydroperoxysilanes, preparation, 783 Alkyl hydrotrioxides, structural chemistry, 132 Alkyl iodides, dioxirane oxidation, 1158 Alkyl methyl sulfonates, alkyl hydroperoxide synthesis, 673... 

The syntheses of iron isonitrile complexes and the reactions of these complexes are reviewed. Nucleophilic reagents polymerize iron isonitrile complexes, displace the isonitrile ligand from the complex, or are alkylated by the complexes. Nitration, sulfonation, alkylation, and bromina-tion of the aromatic rings in a benzyl isonitrile complex are very rapid and the substituent is introduced mainly in the para position. The cyano group in cyanopentakis(benzyl isonitrile)-iron(ll) bromide exhibits a weak "trans" effect-With formaldehyde in sulfuric acid, benzyl isonitrile complexes yield polymeric compositions. One such composition contains an ethane linkage, suggesting dimerization of the transitory benzyl radicals. Measurements of the conductivities of benzyl isonitrile iron complexes indicate a wide range of A f (1.26 e.v.) and o-o (1023 ohm-1 cm.—1) but no definite relationship between the reactivities of these complexes and their conductivities. 

Tallow soap or sodium stearate Sodium dodecyl benzene sulfonate Alkyl naphthal trimethyl ammonium... 

The composition data obtained for the series of mixed fatty acid-potassium soap systems, prepared by both the ethanol and petroleum ether routes, lend strong support to the formation of 1 to 1 acid-soap complexes. It is of interest to inquire into the phase relationships in these two-component systems. A phase diagram presented by McBain and Field (15) for the lauric acid-potassium laurate system shows that compound formation takes place between the two components at the 1 to 1 molar ratio, but the compound undergoes melting with decomposition at 91.3 °C. [A similar type of phase behavior has been reported by us for the sodium alkyl sulfate-alkyl alcohol (9) and sodium alkyl sulfonate-alkyl alcohol (12) systems, but in these cases the stoichiometry is 2 to 1]. 

Although essentially pure soap products continue lo dominate the cleansing-bar field, a few products contain synthetic surfactams in addition 10 soap to act as scum and curd dispersants. Synthetic surfactants used in this application include alkyl sulfates, alkyl glyceryl ether sulfonates, alkyl esters of sodium isothionale. and alkylamides of N-melhyl tauride. 

---