Synthesis of Thiiranes by Direct Sulfur Transfer:  The Challenge of Developing Effective Sulfur Donors and Metal Catalysts

Adam, Waldemar; Bargon, Rainer M.

doi:10.1021/cr030005p

Cited by 72 publications

(44 citation statements)

References 95 publications

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“…Elemental sulfur without chemical activation was used successfully in the synthesis of thiiranes from the corresponding alkenes only in a few examples . Heating syn ‐bibenzonorbornenylidene syn ‐ 1 with elemental sulfur in refluxing o ‐dichlorobenzene led exclusively to episulfide syn ‐ 2 in 83% yield with retention of the configuration (Scheme ) .…”

Section: Sulfur As Building Block – Sulfuration Reactionsmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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Elemental sulfur hasb een known since Antiquity and found widespread applications in the preparation of black gunpowder,t he synthesis of sulfuric acid as well as other sulfur-containing compounds,a nd the vulcanization of rubber.O ver the last several years,wehave come to better understand its properties andd iscover more applications of elementals ulfuri ns ynthetic organic chemistry.T his review summarizes the advancesf rom 2000i nt he construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

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Section: Sulfur As Building Block – Sulfuration Reactionsmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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“…Thiirane or episulfide is a well-known functionality in organic synthesis and it is widely prepared by using various synthetic procedures [27][28][29][30][31][32][33][34]. Initially to make thiirane, soy fatty acid methyl esters were treated with elemental sulfur in various solvents, such as THF and dimethyl formamide (DMF), under reflux conditions up to 1208C.…”

Section: Synthesis Of Thiirane and Epoxy Thiirane Fatty Acid Methyl mentioning

confidence: 99%

Functionalization of soy fatty acid alkyl esters as bioplasticizers

Kandula

Stolp

Graß

et al. 2015

Vinyl Additive Technology

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The combination of various functional groups, such as epoxy, acetoxy, methoxy, thiirane, and aziridine, on the fatty acyl chain of soy fatty acid alkyl esters have been synthesized and evaluated as plasticizers in poly(vinyl chloride) (PVC) applications. Numerous synthetic procedures, such as epoxidation, methoxylation, acetylation, thiiration, and aziridination, were used for synthesizing multifunctional soy fatty acid alkyl esters. Epoxidized soybean oil fatty acid alkyl ester served as the key intermediate for functionalization. Partial or complete ring opening of the epoxide by reacting with methanol and the subsequent etherification or acetylation of the hydroxyl function produced epoxy, alkoxy, and acetoxy derivatives. The nucleophilic substitution of epoxide with sulfur by reacting with ammonium thiocyanate produced thiirane and epoxy thiiranes. Although the aziridine derivatives were synthesized by reacting unsaturated fatty acid alkyl esters with chloramine-T, the compounds were fully characterized and their physical and analytical properties were determined. The high viscosity and darker color of aziridine and thiirane derivatives limit their usefulness, whereas the physical properties of the other derivatives were acceptable. The plasticizer evaluation of methoxy and acetoxy soy fatty acid esters (methyl and n-butyl) demonstrated good compatibility with PVC, high efficiency (Shore hardness), and gelling properties were comparable to commercial plasticizer, di-isoonyl phthalate. The abundant availability and cost-effectiveness of starting materials and the readily adoptable chemical processes make the fatty acid ester derivatives viable bioplasticizers to replace the fossil fuel-derived phthalates. J. VINYL ADDIT. TECH-

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“…This is, however, not the case. The few direct methods have been nicely summarized in a recent review [692]. Nevertheless, there are some protocols that merit special attention.…”

Section: From Alkenesmentioning

confidence: 99%

Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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Synthesis of Thiiranes by Direct Sulfur Transfer: The Challenge of Developing Effective Sulfur Donors and Metal Catalysts

Cited by 72 publications

References 95 publications

Recent Advances in Organic Reactions Involving Elemental Sulfur

Recent Advances in Organic Reactions Involving Elemental Sulfur

Functionalization of soy fatty acid alkyl esters as bioplasticizers

Three‐Membered Heterocycles. Structure and Reactivity

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