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Synthesis of Disulfides - Organic chemistry

Sharpless, Bifluoride-catalysed sulfur(VI) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates.

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Categories: S-S Bond Formation > Synthesis of Disulfides

Sharpless, A Click Chemistry Approach to Tetrazoles by Huisgen 1,3-Dipolar Cycloaddition: Synthesis of 5-Sulfonyl Tetrazoles from Azides and Sulfonyl Cyanides,

Sharpless, Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

AB - The synthesis of a variety of symmetrical bis(alkyl) and bis(fluoroalkyl) disulfides as well as mixed alkyl fluoroalkyl disulfides containing ester or amide groups is described. Self-assembled monolayers of these compounds on gold formed by spontaneous adsorption from solution are studied by contact angle measurements and polarized grazing incidence Fourier transform infrared spectroscopy (FTIR). The contact angles indicate tight packing of the molecules and the incorporation of both alkyl and fluoroalkyl chains in the monolayers. By means of FTIR, the typical tilted orientation of the alkyl chains is confirmed for monolayers derived from symmetrical alkyl disulfides, whereas, in self-assembled monolayers of the symmetrical fluorocarbon and the mixed disulfides, the molecules are oriented much closer to the surface normal direction. The wetting properties and the FTIR spectra of monolayers formed by coadsorption of an n-alkanethiol and a perfluorinated thiol are comparable to those formed by the self-assembly of the corresponding mixed disulfide. There is no indication for phase separation in any of the systems studied at room temperature. The mixed alkyl fluoroalkyl disulfides promise to form suitable monolayers on gold for the investigation of heat-induced phase separation on the gold surface.

Synthesis of sulfonyl chlorides - Organic chemistry

Fokin, SuFEx-Based Synthesis of Polysulfates, , 53 (36), 9466-70 (2014).

Sharpless, A Heck-Matsuda Process for the Synthesis of -Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.

The initiating sites are preserved within the core of the star polymer (i.e., alkyl halide groups in ATRP) and the (polyA)n-polyX star polymer can be used as a multifunctional star initiator in a chain extension reaction with a different monomer, B, to yield a miktoarm star copolymer, (polyA)n-polyX-(polyB)m. This combination method for synthesizing miktoarm star copolymers was termed the "in-out" method.(28,30)The efficiency of initiation of the second set of arms is dependent on the compactness of the first formed core with less densely crosslinked cores providing more efficient initiation i.e., a greater fraction of the encapsulated initiator sites, for the grafting out polymerization.(31)Normally, one seeks to, or has to, form a chemically stable core. However, it is possible to select a crosslinking agent with a degradable link between the two functional crosslinking groups and prepare a material with a degradable core.This was accomplished by linking the first formed arms with a dimethacrylate crosslinker containing a disulfide link between the methacrylate units. As shown in the above scheme the mikto-arm star copolymer could be degraded in a reducing environment to form a mixture of an AB block copolymer and some residual A-homopolymer. The ratio between the block copolymer and homopolymer gave a direct measurement of the initiating efficiency of the constrained core initiating units; in this example it was only ~20%.(30) We recently reported a new strategy for synthesis of miktoarm star copolymers using a simple and general "arm-first" method, i.e., one-pot ATRP cross-linking a mixture of different linear MIs and/or MMs with a divinyl cross-linker in order to synthesize miktoarm star copolymers with potentially any desired molar ratio and composition of the arms.(35,37)Liquid chromatography under the critical conditions (LCCC) for each of the homopolymers arms provided proof that the star structure a miktoarm star copolymer containing two or more compositionally different arm species in one molecule, and was not a mixture of different homo-arm star polymers.(35) Miktoarm star copolymers containing five kinds of arms were synthesized for the first time by copolymerizing a mixture of five linear MIs with different chemical composition.

Synthesis and Study of Dialkylbenzyl Disulfides,

Chang, Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity,

T1 - Self-Assembled Monolayers of Symmetrical and Mixed Alkyl Fluoroalkyl Disulfides on Gold. 1. Synthesis of Disulfides and Investigation of Monolayer Properties

N2 - The synthesis of a variety of symmetrical bis(alkyl) and bis(fluoroalkyl) disulfides as well as mixed alkyl fluoroalkyl disulfides containing ester or amide groups is described. Self-assembled monolayers of these compounds on gold formed by spontaneous adsorption from solution are studied by contact angle measurements and polarized grazing incidence Fourier transform infrared spectroscopy (FTIR). The contact angles indicate tight packing of the molecules and the incorporation of both alkyl and fluoroalkyl chains in the monolayers. By means of FTIR, the typical tilted orientation of the alkyl chains is confirmed for monolayers derived from symmetrical alkyl disulfides, whereas, in self-assembled monolayers of the symmetrical fluorocarbon and the mixed disulfides, the molecules are oriented much closer to the surface normal direction. The wetting properties and the FTIR spectra of monolayers formed by coadsorption of an n-alkanethiol and a perfluorinated thiol are comparable to those formed by the self-assembly of the corresponding mixed disulfide. There is no indication for phase separation in any of the systems studied at room temperature. The mixed alkyl fluoroalkyl disulfides promise to form suitable monolayers on gold for the investigation of heat-induced phase separation on the gold surface.

Sharpless, Synthesis of Vicinal Diamines from Cyclic Sulfates, , 36, 9241 (1995).
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