Synthesis of organochalcogen compounds in basic reducing systems

Deryagina, É. N.; Russavskaya, N. V.; Papernaya, L. K.; Леванова, Е. П.; Sukhomazova, E. N.; Корчевин, Н. А.

doi:10.1007/s11172-006-0143-0

Cited by 31 publications

(7 citation statements)

References 44 publications

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“…Elemental sulfur could be transformed into the anionic form S n 2− when treated with a mixture of hydrazine hydrate and KOH (Scheme ) . Elemental sulfur was reduced with the formation of potassium polysulfides in which the value of n is determined by the KOH:sulfur molar ratio.…”

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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“…35 Hydrazine has also been used in combination with alkaline media in the synthesis of organochalcogen compounds. 36 As a strong reducing agent, hydrazine is well known and it can reduce many ions to their lower oxidation states or even to the bare metal or hydride states. Most elements thus only exist at their lower oxidation state in hydrazine (e.g., Cu exists as Cu I ).…”

Section: Solvent Properties Of Hydrazinementioning

confidence: 99%

Solvent properties of hydrazine in the preparation of metal chalcogenide bulk materials and films

Yuan¹,

Mitzi²

2009

Dalton Trans.

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A combination of unique solvent properties of hydrazine enables the direct dissolution of a range of metal chalcogenides at ambient temperature, rendering this an extraordinarily simple and soft synthetic approach to prepare new metal chalcogenide-based materials. The extended metal chalcogenide parent framework is broken up during this process, and the resulting metal chalcogenide building units are re-organized into network structures (from 0D to 3D) based upon their interactions with the hydrazine/hydrazinium moieties. This Perspective will review recent crystal and materials chemistry developments within this family of compounds and will briefly discuss the utility of this approach in metal chalcogenide thin-film deposition.

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“…Such "reductive activation" is effectively carried out, for example, in basicreductive systems based on hydrazine hydrate, which can also be employed for the reductive cleavage of disulfides. 7 During the reaction, hydrazine hydrate is converted into nitrogen and water, which is an advantage in the development of industrially oriented synthetic methods. The sulfur anions S 2À , S 2 2À , or thiolate anions RS À formed via the reduction of elemental sulfur or diorganyl disulfides are involved in situ into the interaction with organic electrophiles, most often halogen-containing ones (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Reactivity of bis(2‐chloroprop‐2‐enyl)sulfide in the system hydrazine hydrate/alkali: A quantum chemical insight

Teplyashin

Bobkov

Корчевин

et al. 2023

J of Physical Organic Chem

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The reactivity of bis(2‐chloroprop‐2‐enyl)sulfide in the system hydrazine hydrate/alkali has been studied using quantum‐chemical methods. The B2PLYP‐D2//B3LYP approach shows a good agreement between the relative values of activation barriers compared to high‐precision CBS//Q‐B3. The correction for the entropy change during the transition from the gas phase to the binary solvent hydrazine hydrate is calculated. The IEF PCM model was parameterized for hydrazine hydrate solvent. The studied reaction routes includes (i) a competition between migration of the C=C bond and dehydrochlorination of bis(2‐chloroprop‐2‐enyl)sulfide; (ii) 1,3‐prototropic rearrangements of bis (allenyl)sulfide resulting from a dehydrochlorination; (iii) the possible substitution of sulfur and chlorine atoms with hydrazine. The probable formation of the thiiranium and thiirenium cations formation in the above has also been evaluated.

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Synthesis of organochalcogen compounds in basic reducing systems

Abstract: The review surveys the data on the synthesis of organosulfur, selenium, and tellurium compounds in basic reducing systems. Good prospects of the hydrazine hydrate-alkali system are demonstrated.

Cited by 31 publications

References 44 publications

Recent Advances in Organic Reactions Involving Elemental Sulfur

Recent Advances in Organic Reactions Involving Elemental Sulfur

Solvent properties of hydrazine in the preparation of metal chalcogenide bulk materials and films

Reactivity of bis(2‐chloroprop‐2‐enyl)sulfide in the system hydrazine hydrate/alkali: A quantum chemical insight

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