60601-05-0Relevant articles and documents
SULFINIC ACIDS AND RELATED COMPOUNDS. 22. DERIVATIVES OF 2-HYDROXYETHANE-SULFINIC ACID
Lee, Chew,Stidham, D. Brian,Field, Lamar
, p. 53 - 59 (2007/10/02)
Sodium 2-hydroxyethanesulfinate (3) could be converted to the unstable methyl ester 8 by acidification followed by reaction with diazomethane (although the acid 4, itself, could not be isolated as reported).The ester 8 was esterified with 2,2'-dithioacetyl dichloride (10) to afford the desired convergent synthesis of a disulfide bissulfinate ester (11), but 11 was even less stable than 8; efforts to esterify the sulfinate salt 3 with 10 to give a more stable sulfinate salt counterpart (12) of the ester 11 were unpromising.The salt 12 also was sought by reduction of a sulfonyl chloride 13, which was obtained by coupling 10 with 2-hydroxyethanesulfonyl chloride (2) and for which the structure was confirmed by reaction with p-bromoaniline; 12 evidently was obtained, but greater purity not be obtained than ca. 83-95percent.In other reactions, 2-hydroxyethanesulfonyl chloride (2) reacted with p-bromoaniline, and the hydroxysulfonanilide (6) produced could be esterified with 10 to give 9 by use of special conditions.
Primary Processes in the Reaction of OH-Radicals with Sulphoxides
Veltwisch, Dieter,Janata, Eberhard,Asmus, Klaus-Dieter
, p. 146 - 153 (2007/10/02)
The primary processes in the OH radical-induced oxidation mechanism of sulphoxides have been investigated by pulse radiolysis and, in particular, by an improved conductivity detection method with time resolution of ca. 50 ns in aqueous solution.Electrophilic addition of the OH radical to the sulphoxide group leads to a transient adduct, R2SO(OH) which decays unimolecularly with t0.5 up to 100 ns into a sulphinic acid, RSO2H, and a radical R.The various RSO2H have been identified by their pKa, and R (including t-butyl and phenyl radicals) by direct optical measurement or chemical scavenging experiments.The probability of radical split off from R2SO(OH) for mixed sulphoxides depends on the stability of the radical leaving.Depending on the nature of the sulphoxide substituents two other OH radical reactions compete with, and may even predominate over, the addition at the sulphoxide group.Thus hydrogen-atom abstraction readily occurs from longer chain and branched aliphatic groups and in the presence of aromatic substituents OH radicals add to the ?-system to form a hydroxycyclohexadienyl radical.The respective yields, kinetics and some physico-chemical properties of the primary species are presented and discussed.