Synthesis of 3,5-dialkyl-1,2,4-trithiolanes

Tjan, S.B.; Haakman, J. C.; Teunis, C.J.; Peer, H. G.

doi:10.1016/0040-4020(72)88110-9

Cited by 39 publications

(13 citation statements)

References 14 publications

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“…The upper layer was filtered over SiO 2 60 (30 g), and the filtrate was concentrated in vacuo to provide 3.32 g of a brownish oil containing 3,5-dimethyl-1,2,4-trithiolane (20% trans-1, 21% cis-1 by GC), 3,6-dimethyl-1,2,4,5-tetrathiane (27% trans-2, 25% cis-2 by GC), 4,6-dimethyl-1,2,3,5-tetrathiane (2%/1% trans-3/cis-3 by GC 1 )), as well as 4,7-dimethyl-1,2,3,5,6-pentathiepane (7%/7% trans/cis-4 by GC 1 )). The NMR data of cis-1 and trans-1 are in very good agreement with those from literature [21].…”

Section: Experimental Partsupporting

confidence: 86%

High‐Impact Sulfur Compounds: Constitutional and Configurational Assignment of Sulfur‐Containing Heterocycles

Krafft

Brennecke

Ott

et al. 2008

Chemistry & Biodiversity

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To unambiguously identify their structures and to evaluate their organoleptic properties, several constitutional und configurational isomers of dialkyl-tetrathianes and dialkyl-pentathiepanes were synthesized by two different synthetic protocols, and separated by preparative gas chromatography. Raman and NMR spectroscopy were used to differentiate between the constitutional 3,6-dialkyl-1,2,4,5-tetrathiane and the 4,6-dialkyl-1,2,3,5-tetrathiane isomers. Furthermore, cis- and trans-isomers of 3,6-dialkyl-1,2,4,5-tetrathianes were distinguished by temperature-dependent NMR experiments. Static, quantum-chemical simulations of the NMR spectra for these cis- and trans-isomers were calculated in the gas layer in order to confirm our experimental assignments. In addition, the assignment of 4,7-alkyl-1,2,3,5,6-pentathiepanes were deducted from their Raman spectra. Dialkyl-tetrathianes and dialkyl-pentathiepanes are interesting components to be used in flavor applications due to their unique olfactory impact and facets.

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Section: Experimental Partsupporting

confidence: 86%

High‐Impact Sulfur Compounds: Constitutional and Configurational Assignment of Sulfur‐Containing Heterocycles

Krafft

Brennecke

Ott

et al. 2008

Chemistry & Biodiversity

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“…As is shown herein,6 the situation is completely different in the sulfur series. 1,2,4‐Trithiolane ( 3 ) is a stable, easily accessible substance 7. There are additional reasons to try the thermal fragmentation of 3 into the title molecule 2 , the analogue of Criegee's “zwitterion”, and thioformaldehyde ( 4 ).…”

Section: Calculated (B3lyp/6‐311+g(3df3pd) Harmonic Approximation; mentioning

confidence: 99%

ThioformaldehydeS-sulfide (Thiosulfine)

Mlostoń

Romański

Reisenauer

et al. 2001

Angew. Chem. Int. Ed.

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“…Enolizable ketones and aldehydes can be converted efficiently into the corresponding alkylated 1,2,4‐trithiolanes using Asinger's method, which consists in the treatment of the carbonyl compounds with H 2 S, secondary amines, and elemental sulfur ,. [16a] In the case of aldehydes, mixtures of cis ‐ and trans ‐3,5‐dialkyl‐1,2,4‐trithiolanes are formed.…”

Section: Methods For the Preparation Of 124‐trithiolanesmentioning

confidence: 99%

Organic and Coordination Chemistry of 1,2,4‐Trithiolanes

et al. 2019

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The review is aimed in summarizing the most important aspects of the chemistry of 1,2,4‐trithiolanes, which form a relevant class of cyclic polysulfides abundant in nature. Some of them were identified as components of Lenthinus edodes (shiitaki mushrooms) extracts as well as of Parkia speciosa (stink bean), which are well known in Asian cuisine. In addition, they determine the flavor of boiled beef and roasted chicken. Thermal decomposition of 1,2,4‐trithiolanes, either in solution or in the gas phase, results in [3+2]‐cycloelimination leading to the release of reactive thiocarbonyl S‐sulfides existing in equilibrium with sulfur‐rich, three‐membered dithiiranes. Both, 1,2,4‐trithiolanes and the products of their decomposition react with low‐valent platinum and iron compounds forming the corresponding sulfur‐metal complexes. For example, iron‐sulfur clusters formed in these reactions are of interest as structural models of [Fe,Fe]‐hydrogenase mimics.

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Synthesis of 3,5-dialkyl-1,2,4-trithiolanes

Cited by 39 publications

References 14 publications

High‐Impact Sulfur Compounds: Constitutional and Configurational Assignment of Sulfur‐Containing Heterocycles

High‐Impact Sulfur Compounds: Constitutional and Configurational Assignment of Sulfur‐Containing Heterocycles

ThioformaldehydeS-sulfide (Thiosulfine)

Organic and Coordination Chemistry of 1,2,4‐Trithiolanes

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