ChemInform Abstract: ORGANOSCHWEFELVERBINDUNGEN 6. MITT. DARST. VON CARBAMOYLESTERN AROMATISCHER DITHIOSAEUREN UND IHRE SPEKTRALEN EIGENSCHAFTEN

Katō, Shinzi; Mitani, Tsuyoshi; Mizuta, Masateru

doi:10.1002/chin.197311250

Cited by 2 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To our knowledge, no crystal analysis of ammonium dithiocarboxylates has been reported. Since the first isolation of crystalline ammonium dithiocarboxylates in 1972, a variety of ammonium dithiocarboxylates have been prepared. − However, quaternary ammonium dithiocarboxylate has been limited to only tetramethylammonium 2-methylpropanecarbodithioate and benzenecarbodithioate and tetraethylammonium 2-hydroxybenzenecarbodithioate 43 and tetrathiooxalates, most likely due to the difficulty of preparation and purification. Their X-ray structural analyses have not been described.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Heavy Alkali Metal Arenedithiocarboxylates: A Facile Synthesis, Dimeric Structure, and Nonbonding Interaction between the Metals and Aromatic Ring Carbons

et al. 1999

Self Cite

View full text Add to dashboard Cite

Dithiocarboxylic acids and their trimethylsilyl esters were found to readily react with potassium, rubidium, and cesium fluorides to give the corresponding alkali metal dithiocarboxylates 3-5 in moderate to good yields. A series of tetramethylammonium dithiocarboxylates 8 have been prepared in good yields by the reaction of sodium dithiocarboxylates 7 with tetramethylammonium chloride. The structures of potassium (3b), rubidium (4g), cesium (5f), and tetramethylammonium 4-methylbenzenecarbodithioates (8e) and tetramethylammonium 2-methoxybenzenecarbodithioate (8f) were characterized crystallographically. These heavier alkali metal salts (3b, 4g, 5f) have a dimeric structure [(RCSSM)(2), M = K, Rb, Cs] in which the two dithiocarboxylate groups are chelated to the metal cations which are located on the upper and lower sides of the plane involving the two opposing dithiocarboxylate groups. The K(+) cations interact with the tolyl fragment of a neighboring molecule, while the Rb(+) and Cs(+) cations interact with two neighboring tolyl fragments, in which the ipso and ortho carbons are positioned close to the metals. The interaction number of the metals with surrounding atoms is 8 for K(+) and Rb(+) and 12 for Cs(+). The C-S distances of the dithiocarboxylate group are different for the potassium salt 3b. In contrast, those of the rubidium salt 4g and cesium salt 5f are equal. Similarly, the chelating sulfur-metal bond distances of 3b are different, while those of 4g and 5f are almost equal. The dihedral angles of the phenyl ring and dithiocarboxylate plane increase in the order of the K, Rb, and Cs salts. The structural analysis of sodium 4-methylbenzenecarbodithioate (7g) revealed the presence of 4-CH(3)C(6)H(4)CS(2)Na(0.36). In contrast, the tetramethylammonium salts 8 are monomeric where the cation moieties are located out of the dithiocarboxylate plane. The potassium 3, rubidium 4, and cesium dithiocarboxylates 5 readily reacted with methyl iodide or triorganotin chlorides at room temperature to give the corresponding methyl 9 and triorganotin dithioesters 10 in good yields. At 0 degrees C, the reactivity of the rubidium 4 and cesium salts 5 to methyl iodides decreases dramatically compared with those of the sodium salts 7 and potassium salts 3.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Materials. Dithiocarboxylic acids 2 were prepared by acidolysis of the corresponding piperidinium dithiocarboxylates 38,39 with concentrated hydrogen chloride. Trimethylsilyl dithiocarboxylates 1 46 and lithium 6 6b and sodium dithiocarboxylates 7 6a were prepared by the method described in the literature.…”

Section: Methodsmentioning

confidence: 99%

Heavy Alkali Metal Arenedithiocarboxylates: A Facile Synthesis, Dimeric Structure, and Nonbonding Interaction between the Metals and Aromatic Ring Carbons

et al. 1999

Self Cite

View full text Add to dashboard Cite

show abstract

“…Such piperidinium salts are powerful nucleophiles,14 although to a lesser degree than tetraalkylammonium salts,15,16 and were used to give tetrathioterephthalic esters. 13,14,17 We have synthetised DMTT in a one-pot procedure and obtained reproducible yields in the range 45-50% by reacting l,4-bis(chloromethyl)benzene with elemental sulfur in methanol (600 mL/0.1 mol of dichloride) and alkylating the sodium salt with dimethyl sulfate (Scheme I). Yields are lowered if less solvent is used.…”

Section: Monomer Synthesismentioning

confidence: 99%

Polythioamide and poly(1,3,4-thiadiazole) synthesis from dimethyl tetrathioterephthalate

Delfanne¹,

Lévesque²

1989

Macromolecules

View full text Add to dashboard Cite

ChemInform Abstract: ORGANOSCHWEFELVERBINDUNGEN 6. MITT. DARST. VON CARBAMOYLESTERN AROMATISCHER DITHIOSAEUREN UND IHRE SPEKTRALEN EIGENSCHAFTEN

Abstract: Die Dithiobenzoesäuren (I) reagieren mit den Phenylisocyanaten (II) zu den gemischten Thioanhydriden (III).

Cited by 2 publications

References 1 publication

Heavy Alkali Metal Arenedithiocarboxylates: A Facile Synthesis, Dimeric Structure, and Nonbonding Interaction between the Metals and Aromatic Ring Carbons

Heavy Alkali Metal Arenedithiocarboxylates: A Facile Synthesis, Dimeric Structure, and Nonbonding Interaction between the Metals and Aromatic Ring Carbons

Polythioamide and poly(1,3,4-thiadiazole) synthesis from dimethyl tetrathioterephthalate

Contact Info

Product

Resources

About