Untitled

Timokhina, L. V.; Panova, G. M.; Kanitskaya, L. V.; Sokol'nikova, O. V.; Toryashinova, D. S. D.; Воронков, М. Г.

doi:10.1023/a:1013837026547

Cited by 3 publications

(15 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 1 H NMR spectra (CDCl 3 , δ, ppm) show signals at 3.96 s (2H, CH 2 ) (for 13), 4.32 s (2H, CH 2 ) (for 14), 7.08-8.35 m (1H, NH and 10H, H arom.). 13 C NMR spectra (CDCl 3 , δ C , ppm) exhibit signals at 38.01 (CH 2 ) (for 13), 39.05 (CH 2 ) (for 14).…”

Section: Methodsmentioning

confidence: 99%

“…Conjugated thioketones 23 permit the synthesis of dithiodimedone, a representative of a rare type of compounds, β-dithiodiketones [30]. 5,5-Dimethyl-3-mercaptocyclohex-2-ene-1-thione (40) has been prepared in quantitative yield by the thiolysis of 23b-f with sodium hydrosulfide or sodium sulfide in an inert atmosphere at 0-20 • C in methanol (scheme 17). Compound 40 has also been obtained in the reaction of dimedone 41 with hydrogen sulfide in alcohol in the presence of hydrogen chloride at −50 • C (35% yield) (scheme 17) [30].…”

Section: Chemical Propertiesmentioning

confidence: 99%

“…A systematic study of synthetic routes to 1,7-dithioxo-substituted systems containing the structural fragment S=C−C=C−S−C=C−C=S has been carried out [11,39]. With this goal the hydrothiolysis of immoniothioxo-, immoniooxo-and bisimmonio-substituted α, β-unsaturated sulfides of the propenic, cyclohexenic and indenic series have been investigated.…”

Section: 7-dithioxo-substituted Systems S=c−c=c−s−c=c−c=smentioning

confidence: 99%

“…Methods for the synthesis of previously unknown carbofunctional symmetrical and unsymmetrical α, β-unsaturated sulfides, potential precursors of 1,7-dithiocarbonyl compounds and their mono oxygen analogs, have been elaborated [40][41][42].…”

Section: Synthesis Of Immonium Salts -Precursors Of 17-dithiocarbonymentioning

confidence: 99%

“…3-Bromo-2-phenylinden-1-one (51) in the presence of perchlorate anion reacts with the thiocarbonyl group of 3-N ,N -dimethylamino-1-phenylprop-2-ene-1-thione (52), 5,5-dimethyl-3-morpholinocyclohex-2-ene-1-thione (24d), 3-N ,Ndimethylamino-2-phenylindene-1-thione (37a) under mild conditions (methanol, 40 • C) to form 1-N,N-dimethylimmonio-3-phenylprop-2-en-3-yl 1-oxo-2-phenylinden-3-yl sulfide perchlorate (53) (72%), 5,5-dimethyl-3-morpholiniocyclohex-2-en-3-yl 1-oxo-2-phenylinden-3-yl sulfide perchlorate (54) (98%), and 1-N ,N -dimethylimmonio-2-phenylinden-3-yl 1-oxo-2-phenylinden-3-yl sulfide perchlorate (55) (79%), respectively (scheme 23) [40].…”

Section: Scheme 23mentioning

confidence: 99%

See 4 more Smart Citations

Thiocarbonyl compounds from β-substituted vinylald- and -ketimmonium derivatives

Timokhina¹,

Воронков²

2004

Journal of Sulfur Chemistry

View full text Add to dashboard Cite

Section: Methodsmentioning

confidence: 99%

Section: Chemical Propertiesmentioning

confidence: 99%

Section: 7-dithioxo-substituted Systems S=c−c=c−s−c=c−c=smentioning

confidence: 99%

Section: Synthesis Of Immonium Salts -Precursors Of 17-dithiocarbonymentioning

confidence: 99%

Section: Scheme 23mentioning

confidence: 99%

See 3 more Smart Citations

Thiocarbonyl compounds from β-substituted vinylald- and -ketimmonium derivatives

Timokhina¹,

Воронков²

2004

Journal of Sulfur Chemistry

View full text Add to dashboard Cite

ChemInform Abstract: 1,7‐Dithioxo Systems. Synthetic Routes to Bis(5,5‐dimethyl‐3‐thioxo‐1‐cyclohexenyl) Sulfide.

et al. 2002

View full text Add to dashboard Cite

2002cyclohexane derivatives cyclohexane derivatives Q 0040 28 -105 1,7-Dithioxo Systems. Synthetic Routes to Bis(5,5-dimethyl-3-thioxo-1-cyclohexenyl) Sulfide.-Attempts for alternative synthetic routes to the title compound (I) failed. It was found that the best procedure is an already reported one. -(TIMOKHINA, L. V.; PANOVA, G. M.; KANITSKAYA, L. V.; SOKOL'NIKOVA, O. V.; TORYASHINOVA, D.-S. D.; VORONKOV, M. G.; Russ.

show abstract

1,7-dithioxo systems. Reaction of 3-[(5,5-dimethyl-3-thioxocyclohex-1-en-1yl)sulfanyl]-5,5-dimethylcyclohex-2-ene-1-thione with 2-aminoethanol and ethane-1,2-diamine

Timokhina

Kanitskaya

2009

Russ J Org Chem

Self Cite

View full text Add to dashboard Cite

The reaction of 3-[(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl)sulfanyl]-5,5-dimethylcyclohex-2-ene-1-thione with 2-aminoethanol involves cleavage of the sulfide bond with formation of 3-[(2-hydroxyethyl)-amino]-5,5-dimethylcyclohex-2-ene-1-thione as the major product. The reaction of the same sulfide with ethane-1,2-diamine gave previously unknown 3-({2-[(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl)amino]ethyl}-amino)-5,5-dimethylcyclohex-2-ene-1-thione.In continuation of our studies on the chemical properties of compounds containing an S=CC=CSC=CC=S fragment [1,2], in the present work we examined reactions of 3-[(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl)sulfanyl]-5,5-dimethylcyclohex-2-ene-1-thione (I) with N,O-and N,N-binucleophiles. The reactions of dithioxo sulfide I with 2-aminoethanol and ethane-1,2-diamine were carried out in acetonitrile in an inert atmosphere. Like aminolysis of compound I reported previously [2], these reactions involved cleavage of the sulfide bond in the substrate.The reaction of I with 2-aminoethanol resulted in the formation of 3-[(2-hydroxyethyl)amino]-5,5-dimethylcyclohex-2-ene-1-thione (II) as the major product (Scheme 1). Enamino thioketone II was synthesized previously by reaction of 2-aminoethanol with 3-methoxy-5,5-dimethylcyclohex-2-ene-1-thione [3]. In the present article we report for the first time detailed spectral parameters of compound II. Its 1 H NMR spectrum contained signals at δ 6.49 ppm typical of =CH protons and NH signal at δ 8.08 ppm; protons of the methylene groups in the CH 2 CH 2 OH fragment resonated at δ 3.39 and 4.74 ppm, respectively, and broadened signal at δ 4.84 ppm was assigned to the hydroxy proton. In the 13 C NMR spectrum of II, the CH 2 OH signal was located at δ C 58.62 ppm, and the =C-N carbon atom gave a signal at δ C 161.48 ppm.Analysis of the 1 H ans 13 C NMR spectra showed that the reaction of dithioxo sulfide (I) with 2-aminoethanol at 20°C, apart from enamino thioketone II, produced a small amount of 3-[(2-{2-[(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl)amino]ethoxy}ethyl)amino]-5,5-dimethylcyclohex-2-ene-1-thione (III).

show abstract

Untitled

Cited by 3 publications

References 3 publications

Thiocarbonyl compounds from β-substituted vinylald- and -ketimmonium derivatives

Thiocarbonyl compounds from β-substituted vinylald- and -ketimmonium derivatives

ChemInform Abstract: 1,7‐Dithioxo Systems. Synthetic Routes to Bis(5,5‐dimethyl‐3‐thioxo‐1‐cyclohexenyl) Sulfide.

1,7-dithioxo systems. Reaction of 3-[(5,5-dimethyl-3-thioxocyclohex-1-en-1yl)sulfanyl]-5,5-dimethylcyclohex-2-ene-1-thione with 2-aminoethanol and ethane-1,2-diamine

Contact Info

Product

Resources

About