The Preparation and Relative Reactivities of Many-Membered Cyclic Disulfides

Affleck, J. G.; Dougherty, Gregg

doi:10.1021/jo01150a024

Cited by 69 publications

(34 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…38 Many approaches have been reported to prepare polymers containing disulfide linkages in the main chain. [39][40][41][42][43][44][45][46] Ringopening polymerization of cyclic disulfide compounds is one method for synthesizing such polymers. Although many studies on the polymerizations of cyclic disulfides were reported since the second half of the 1940s, 39,40 the detailed structural analyses and characterizations of the resulting polymers have not been investigated for a long time.…”

mentioning

confidence: 99%

Ring-Opening Polymerization of Aromatic 6-Membered Cyclic Disulfide and Characterization of the Polymer

Ishida¹,

Kisanuki²,

Endo³

2009

Polym. J.

View full text Add to dashboard Cite

Synthesis and characterization of polymers obtained from polymerization of 1,4-dihydro-2,3-benzodithine (XDS) were investigated. The polymerization of XDS proceeded at reaction temperatures above the melting points of XDS to give polymers, and the molecular weight, which determined by GPC was high. From the structural analysis of poly(XDS), the polymer was found to have cyclic structure, in contrast to their linear polymer (poly(XDS-XDT) obtained from the polymerization of XDS in the presence of chain transfer thiol compounds such as , 0 -mercapto-o-xylene (XDT). From TGA and DSC measurements, poly(XDS) with benzene rings in the main chain is more thermal stable than the polymer obtained from the polymerization of 1,2-dithiane (DT). From dynamic viscoelastic measurements, poly(XDS) showed a rubbery plateau under the molten state even though poly(XDS) has no crosslinking system. The difference in solubility between poly(XDS) and poly(XDS-XDT) was also observed. On the basis of the polymer characterizations, it may be concluded that the poly(XDS) obtained from thermal ring-opening polymerization of XDS includes a polycatenane structure.KEY WORDS: Ring-Opening Polymerization / 1,4-Dihydro-2,3-Benzodithine / Cyclic Polymer / Polycatenane Structure / Cyclic Disulfides / Thermal Decomposition / Recently, much attention has been paid to topologically unique macromolecules containing a single cyclic and multicyclic polymer unit from the viewpoints of not only their distinctive properties that is different from linear polymers, but also elements of architecturally complex polymers and interlocked macromolecules such as polyrotaxanes and polycatenanes.1-11 Many studies on synthesis of cyclic polymers in the polymerizations have been also reported.12-26 Although efficient synthesis of rotaxanes and catenanes have been achieved, 27-37 a high molecular weight polycatenane which consists of only ring components has not been synthesized. Recently, Takata et al. reported that the Diels-Alder polymerization of [2]catenane bearing diene and dienophile moieties on each ring afforded a ''bridged polycatenane'' with a poly[2]catenane skeleton. 38 Many approaches have been reported to prepare polymers containing disulfide linkages in the main chain. [39][40][41][42][43][44][45][46] Ringopening polymerization of cyclic disulfide compounds is one method for synthesizing such polymers. Although many studies on the polymerizations of cyclic disulfides were reported since the second half of the 1940s, 39,40 the detailed structural analyses and characterizations of the resulting polymers have not been investigated for a long time. Recently, we reported the thermal polymerization of 1,2-dithiane (DT) and detailed structural analyses and characterizations of the resulting polymers. From analyses of the polymer, the cyclic structure was formed mainly by a backbiting reaction of propagating species. [44][45][46] We also reported that a polycatenane structure composed of interlocking system by entanglements with cyclic polymers was formed durin...

show abstract

mentioning

confidence: 99%

Ring-Opening Polymerization of Aromatic 6-Membered Cyclic Disulfide and Characterization of the Polymer

Ishida¹,

Kisanuki²,

Endo³

2009

Polym. J.

View full text Add to dashboard Cite

show abstract

“…REACTIVITY, RING CLEAVAGE, AND ULTRAVIOLET ABSORPTION The biological activity of lipoic acid depends on the great reactivity of the disulfide bond of the dithiolane ring. Earlier attempts to interpret this reactivity of (five-membered) lJ2-dithiolanes over the (sixmembered) lJ2-dithianes and open-chain disulfides by the higher strain in the five-membered ring (211), and a calculation of the strain from the shift of the ultraviolet absorption toward longer wavelengths (212,213) were unsuccessful. The strain in the dithiolane ring is only 4-6 kcal/mole (214,215).…”

Section: Chemistry Of A-lipoic Acidmentioning

confidence: 99%

Biochemistry and Chemistry of Lipoic Acids

Schmidt¹,

Grafen²,

Altland³

et al. 1969

Advances in Enzymology - And Related Areas of Molecular Biology

View full text Add to dashboard Cite

“…Other methods for the synthesis of these cyclic disulfides involve a) the reaction of a 1,3-dielectrophile with S 4 2-(followed by the desulfurization with copper [16]), b) the cleavage of a bisthiocyanate with TBAF [17], or c) the steam distillation of an appropriate Bunte salt [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, stereochemistry and adsorption studies of new spiranes and polyspiranes containing 1,2‐dithiolane units

Gropeanu

Tintas

Pilon

et al. 2007

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

S SGold Substrate where R 1 , R 2 = H, methyl, phenyl, 1-naphthyl, or R 1 -R 2 = (un)substituted cyclohexylThe synthesis and stereochemistry of a series of new cyclic disulfides containing (poly)spirane 1,2-dithiolane units are reported. Also included is a study of the self-assembled monolayers (SAMs) of these compounds on a gold surface. The characteristics of the resultant SAMs were determined by IR spectroscopy using molecular mechanics calculations.

show abstract

The Preparation and Relative Reactivities of Many-Membered Cyclic Disulfides

Cited by 69 publications

References 10 publications

Ring-Opening Polymerization of Aromatic 6-Membered Cyclic Disulfide and Characterization of the Polymer

Ring-Opening Polymerization of Aromatic 6-Membered Cyclic Disulfide and Characterization of the Polymer

Biochemistry and Chemistry of Lipoic Acids

Synthesis, stereochemistry and adsorption studies of new spiranes and polyspiranes containing 1,2‐dithiolane units

Contact Info

Product

Resources

About