Disulfides, organic

Nuzzo, R.G. and Allara, D.L. (1983) Adsorption of bifimctional organic disulfides on gold surfaces. Journal of the American Chemical Society, 105, 4481 483. 

To overcome these issues, the water-soluble TCEP was synthesized and successfully used to cleave organic disulfides to sulfhydryls in water (Burns et al., 1991). The advantage of using this phosphine derivative in disulfide reduction as opposed to previous ones is its excellent stability in aqueous solution, its lack of reactivity with other common functionalities in biomolecules, and its freedom from odor. 

AD Aslanov. Organic Disulfides as Inhibitors of Oxidative Processes, Cand. Sci. (Chem.) Thesis Dissertation, Inst. Chem. Phys., Chernogolovka, 1985 [in Russian]. 

Kondo, T., Uenoyama, S.-y., Fujita, K.-i., and Mitsudo, T.-a., First transition-metal complex catalyzed addition of organic disulfides to alkenes enables the rapid synthesis of vicinal dithioethers, /. Am. Chem. Soc., 121, 482, 1999. 

R. C. Nuzzo and D. L. Allara, Adsorption of Bifunctional Organic Disulfides on Gold Surfaces, Journal of American Chemical Society 105, 4481 - 4483 (1983). 

There are three possible types of three-electron bonds. Oxidation of a u bond leads to a cation-radical with a, u three-electron bond. This bond contains no antibonding electrons, and the total bond strength exceeds that of a double bond by the energy of half a n bond. Olefins can acquire the 2a—In bond on one-electron oxidation, the bond constructed from the electrons 2a and In. Oxidation of organic disulfides, RSSR, to their cation-radicals (RSSR) yields species in which the unpaired electron from the oxidized sulfur interacts with the unbound p-electron pair of the second sulfur (Glass 1999). This establishes a 2n-In bond on top of the already existing o bond. The overall bond strength of this five-electron (2a—2n-In ) bond also exceeds that of the normal... 

Irradiation of a mixture of tricydo[4.1.0.02,7]heptane and an organic disulfide in pentane gave 6-alkylsulfanylbicyclo[3.1.1]heptanes 21 as well as mixtures of cis- and PY7w-6,7-dialkylsul-fanylbicyclo[3.3.1]heptanes 22 which were the major products. Somewhat surprisingly, monosulfides were generated almost exclusively when disulfides with bulky alkyl groups were used, presumably due to steric effects.36... 

The arenethiolates [M(SR)3] (R = phenyl or naphthyl) were easily obtained as monomeric soluble products by reductive elimination of organic disulfides from the pentathiolates... 

Organic disulfides can act as monodentate ligands. The simplest compound of this type, dimethyl disulfide, acts as a bridge in [Re2 Br2 (CO)6 (S2 Me2)], where each sulfur coordinates to one Re.18 Other acyclic disulfides have been shown to form complexes of Cu1 and Cu11.18-20 An example incorporating a monodentate cyclic disulfide ligand, the Ru11 complex ion (8), has been reported by Stein and Taube. 2... 

In situ generated acyllithium reagents not only can acylate ketones, but also can acylate aldehydes,3 esters,4 lactones,5 isocyanates and isothiocyanates,6 carbodiimides,7 carbon disulfide and carbonyl sulfide,8 organic disulfides,9 and trialkylchlorosilanes.10 For reviews, see references 11 and 12. This direct, nucleophilic acylation procedure, when applicable, makes unnecessary the usually... 

The water-soluble tris(2-carboxyethyl)phosphine (TCEP) was synthesized and used to cleave rapidly organic disulfides to sulfhydryls in water (Burns et al., 1991). The... 

Although TCEP is capable of rapidly and quantitatively reducing simple organic disulfides in solution, it requires the presence of a deforming agent to reduce fully all disulfides in proteins. Without opening up the internal disulfides in many protein molecules, TCEP will not be able to reduce them. For complete reduction of IgG, it was found that 20 mM TCEP and 5 min of boiling was needed (Hines, 1992). Partial reduction, however, is possible of some more accessible disulfides in aqueous buffers at room temperature. 

Bonifacic M, Schafer K, Mockel H, Asmus K-D (1975b) Primary steps in the reactions of organic disulfides with hydroxyl radicals in aqueous solution. J Phys Chem 79 1496-1502 Bonifacic M, Armstrong DA, Carmichael I, Asmus K-D (2000a) p-Fragmentation and other reactions involving aminyl radicals from amino acids. J Phys Chem B 104 643-649 Bonifacic M, Hug GL, Schoneich C (2000b) Kinetics of the reactions between sulfide radical cation complexes,[S.. S]+ and [S. N]+, and superoxide or carbon dioxide radical anions. J Phys Chem A 104 1240-1245... 

The organic disulfides contain the -SS- functional group, as shown in the following two examples ... 

Organic disulfides and chloroorganic compounds in boundary lubrication conditions form iron sulfide (AHf = -1.04 eV), iron chloride (AHf = -3.54 eV), or iron bromide (AHf = -2.59 eV), which decrease wear and protect against seizure. Some chlorinated and brominated hydrocarbons in the presence of DBDS produce strong synergism in severe conditions involving lubrication in metal cutting (McCarroll et al., 1978 Mould at al., 1973 Plaza, 1989 Plaza et al., 1993 Sakuri etal., 1967). 

Resins carrying the guanidine function have been patented as catalyst[128] for the preparation of organic disulfides and polysulfides11291 and the preparation of sulfonated olefins.[130]... 

Arretz, E., Lopez, F. Method for preparing organic disulfides and polysulfides from mercaptans and sulfur in the presence of heterogeneous styrene-divinylbenzene copolymer catalysts having pendant guanidine or amidine groups. 1996, WO 9721673. 

Addition across S—S and Se—Se bonds. Organic disulfides readily react with propellanes, and the degree of oligomerization depends on the ratio of the reagents . The addition of diacetyl disulfide gives the oligomeric series and provides particularly convenient access to doubly terminal dithiols . The hindered di-r-butyl and dipivaloyl disulfides do not react with la in diethyl ether Diphenyl diselenide reacts with la and yields only the first adduct ... 

Olsson, I., Larsson, K., Palmgren, R. and Bjellqvist, B. (2002) Organic disulfides as a means to generate streak-free two-dimensional maps with narrow range basic immobilized pH gradient strips as first dimension. Proteomics 2, 1630-1632. 

Much of the research on the SbCls-catalyzed halogenation of arenes has focused on the chlorination and bromination of perfluoroalkyl-substituted aromatics [14]. The reaction of organic disulfides with electron-rich aromatic compounds under catalysis with SbCls and AgSbFg affords unsymmetrical aryl sulfides in modest yields [15a]. Electrophilic sulfinylation and sulfonation can be similarly effected by SbCls [15a-c]. Alkyl- and halobenzenes give thiocyano derivatives when treated with a mixture of SbCls and Pb(SCN)2 in CCI4 [16],... 

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