The Preparation of Alkene Trithiocarbonates

Durden, John A.; Stansbury, Harry A.; Catlette, William H.

doi:10.1021/ja01497a026

Cited by 39 publications

(14 citation statements)

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“…There is literature precedent for this reverse Menschutkin reaction 16. 22 The tributylamine can then react with carbon disulfide to form a dithiocarbamate 18 2a,g. h, 24 Complex 11 is in equilibrium with monometallic species 16 .…”

Section: Resultsmentioning

confidence: 99%

Titanium(salen)‐Catalysed Synthesis of Di‐ and Trithiocarbonates from Epoxides and Carbon Disulfide

Beattie

North

2014

ChemCatChem

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The combination of a bimetallic titanium(salen) complex [Ti(salen)O]2 and either tetrabutylammonium bromide or tributylamine forms a highly active catalyst system for the reaction between epoxides and carbon disulfide to lead to di‐ and/or trithiocarbonates. Reactions can be performed at 90 °C by using just 0.5–1.0 mol % of the catalysts. The reactions proceed with the inversion of the epoxide configuration and on the basis of kinetic and spectroscopic evidence, a mechanism to account for the results is proposed.

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Section: Resultsmentioning

confidence: 99%

Titanium(salen)‐Catalysed Synthesis of Di‐ and Trithiocarbonates from Epoxides and Carbon Disulfide

Beattie

North

2014

ChemCatChem

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“…Other thio reagents which are less or not suitable for the synthesis of thiiranes from epoxides include: diphenylthiourea (37), xanthamide, thioacetamide, thiobenzamide, thiobarbituric acid (39). Interaction of alkene oxides with alkali dithioand polythiocarbonates gives cyclic thiocarbonates (37); the same applies to the reaction with carbon disulfide (61,178). Some types of cyclic thiocarbonates can be converted to thiiranes (see section IIB).…”

Section: Introductionmentioning

confidence: 99%

Thiiranes

Sander¹

1966

Chem. Rev.

260

101

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“…[Vol. 41,No. 3 According to the reported method,12) it was determined that this salt contained two molecules of coordinated water.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Reactions of Functional Polymers. XXXIV. Low Polymerization of Ethylene Oxide with Sodium N,N-Dimethyldithiocarbamate in Dipolar Aprotic Solvents

Nakai¹,

Ôkawara²

1968

Bulletin of the Chemical Society of Japan

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The low polymerization of ethylene oxide with sodium dimethyldithiocarbamate in a homogeneous system was studied. This reaction was verified as proceeding through a step-by-step addition mechanism, due to the enhanced nucleophilicity of the dithiocarbamate anion in dipolar aprotic solvents. The solvent effects and the catalyses of various dithiocarbamate salts were also examined. Epichlorohydrin was reacted with this salt in dimethylformamide to afford a polymer with a dithiocarbamate moiety through both ring-opening and substitution processes.

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The Preparation of Alkene Trithiocarbonates

Cited by 39 publications

References 0 publications

Titanium(salen)‐Catalysed Synthesis of Di‐ and Trithiocarbonates from Epoxides and Carbon Disulfide

Titanium(salen)‐Catalysed Synthesis of Di‐ and Trithiocarbonates from Epoxides and Carbon Disulfide

Thiiranes

Synthesis and Reactions of Functional Polymers. XXXIV. Low Polymerization of Ethylene Oxide with Sodium N,N-Dimethyldithiocarbamate in Dipolar Aprotic Solvents

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