Préparation et propriétés de cyclobutanethiones

Paquer, D.; Vazeux, Michel; Leriverend, Pierre

doi:10.1002/recl.19780970502

Cited by 9 publications

(5 citation statements)

References 13 publications

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“…The C=O carbon, as it is expected, appears at the deshielded end (158,5 ppm), while the methoxy carbon, being the most shielded, is seen at 53,1 ppm. As it is seen in the Figure 21, the oxime carbon (C=N) and the cyanide carbon (C≡N) appearing at 127,2 ppm are well separated from each other in the 13 C-NMR spectrum. Due to fast exchange, the oxime proton is not observed in the 1 H-NMR spectrum; however, the methoxy protons are readily identified at 3,79 ppm.…”

Section: Scheme 16: Proposed Mechanism Of the Meyer Reaction In Acidi...mentioning

confidence: 70%

“…These two compounds are convenient representatives to examine thione-thiol tautomerism (Figure 10), hydrogen bonding, acid-base properties as well as spectral characteristics. Practical data of dipole moments, IR, UV, 1 H-NMR, 13 C-NMR, 15 N-NMR spectroscopies and X-ray diffraction confirmed existence of imidazole-2-thiones in the thione form both in the crystalline state and in solution [71] . Especially, the 15 N-NMR data proved that 1-methylimidazole-2-thione in DMSO exists exclusively as the thione tautomer, whereas for benzimidazole-2-thione the equilibrium concentration of the latter is 92% [72] .…”

Section: An Outline Of the Imidazole-2-thione Derivatives 231 Introdu...mentioning

confidence: 78%

“…It was concluded that this finding shall be common to all the thiol/thione tautomerism [12] . Nevertheless, in case of cyclobutanethiones, formation of the enethiol is not favored due to ring strain [13] . Interestingly, it has been also reported that separation of the thiol/thione tautomers might be achieved by vapor-phase chromatography method [14] .…”

Section: Scheme 2: An Example Of the Resonance Effects Of αβ-Unsatura...mentioning

confidence: 99%

“…NMR spectroscopy is especially useful for structural characterization of thiocarbonyl compounds. While 13 C-NMR spectroscopy is utilized to take insights into the nature of the thiocarbonyl carbon because of its characteristic of the extreme low-field position, 1 H-NMR spectroscopy helps to identify the substituents on the thiocarbonyl group and assess quantitatively the thione/enethiol ratio [14] . Actually, compared to carbonyl carbon analogs, the chemical shift of C=S carbon is usually shifted to a lower field by 35-63 ppm that might be very helpful in following as well as controlling the conversion of a carbonyl group into thiocarbonyl one [16] .…”

Section: Scheme 4: the Tautomerism System Of Cyclobutanethionesmentioning

confidence: 99%

“…To achieve similar yield (73-74%), the reaction with ethanolic NaOH in method 1 required higher temperature (100°C) and longer reaction time (4h). Structural identification was performed by IR as well as 13 C-NMR spectroscopies (Figure 23, 24). Again, the functional groups could be readily identified.…”

Section: Scheme 16: Proposed Mechanism Of the Meyer Reaction In Acidi...mentioning

confidence: 99%

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Synthesis, properties and selected applications of some sulfur containing organic compounds

Truong Ngoc

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This work involves sulfur-containing compounds and consists of three studies: 1) Preparation of a sulfur-containing compound, 2-cyano-2-(hydroxyimino)-dithioacetic acid, by a thionation reaction; 2) The secondary interactions (hydrogen bonding) of three imidazole-2-thione derivatives and their aggregation behaviour in solution, the solid state and over polycrystalline gold surface; 3) Synthesis of L-cysteinate-intercalated CaAl-layered double hydroxide (LDH) and study on the interlamellar selective oxidation process of the intercalated L-cysteinate. Chapter 1 contains a few personal reflections as well as a brief statement of the research and aims of the thesis. Chapter 2 of the thesis deals with an entire overview on organosulfur compounds from basic concepts, properties, applications to synthetic methodologies. Contents on thiocarbonyl compounds are also specially emphasized. Next, a brief introduction on imidazole-2-thione derivatives as well as the secondary interactions between these molecules and their self-assembly capacities is described. A concise description on LDHs is also found at the end of chapter. Results of the work including synthesis of 2-cyano-2-(hydroxyimino)-dithioacetic acid; analysis of the secondary interactions (hydrogen bonding) as well as the aggregation behavior of three imidazole-2-thione derivatives in solution, the solid state and over polycrystalline gold surface are reported and discussed in chapter 3. Chapter 3 also includes results on preparation of L-cysteinate-intercalated LDH and examination of selective oxidation of the intercalated cysteinate anions. The first work is an attempt to develop a convenient three-step process for preparation of a ligand in which a thionation reaction is the key step. In the next step, complexation of the resultant ligand with Co(II), Ni(II), Cu(II) ions is scouted. Structural characterization of the intermediates and the ligand were accomplished. In addition, an independent study on the secondary interactions (hydrogen bonding) and self-assembly capacities of three imidazole-2-thione derivatives is also carried out and reported. The work is proceded with results on the synthesis of L-cysteinate-intercalated CaAl-LDH, its structural elucidation and evaluation of selectivity of interlamellar oxidation of the intercalated cysteinate anion to cystinate in aqueous and cysteinate sulfenic acid in acetone. In chapter 4, concluding remarks of the research are summarized. Finally, entire details about experimental work of the thesis including materials, instruments and analytical techniques employed, recipes for preparation of intermediates, ligand and complexes, procedures for synthesis of LDH, the intercalation and oxidation reactions are represented in chapter 5.

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Section: Scheme 16: Proposed Mechanism Of the Meyer Reaction In Acidi...mentioning

confidence: 70%

Section: An Outline Of the Imidazole-2-thione Derivatives 231 Introdu...mentioning

confidence: 78%

Section: Scheme 2: An Example Of the Resonance Effects Of αβ-Unsatura...mentioning

confidence: 99%

Section: Scheme 4: the Tautomerism System Of Cyclobutanethionesmentioning

confidence: 99%

Section: Scheme 16: Proposed Mechanism Of the Meyer Reaction In Acidi...mentioning

confidence: 99%

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Synthesis, properties and selected applications of some sulfur containing organic compounds

Truong Ngoc

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Hydrogen Sulfide

Dittmer

2001

Encyclopedia of Reagents for Organic Synthesis

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ChemInform Abstract: PREPARATION AND PROPERTIES OF CYCLOBUTANETHIONES

Paquer¹,

Vazeux²,

Leriverend³

1978

Chemischer Informationsdienst

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Préparation et propriétés de cyclobutanethiones

Abstract: Abstract. Five substituted cyclobutanethiones were prepared from the corresponding cyclobutanones by sulfurization with hydrogen sulfide, in the presence of hydrogen chloride at 0°C. Spectroscopic data (UV, MS, ' H and I3C NMR) of these new compounds were determined and discussed.

Cited by 9 publications

References 13 publications

Synthesis, properties and selected applications of some sulfur containing organic compounds

Synthesis, properties and selected applications of some sulfur containing organic compounds

Hydrogen Sulfide

ChemInform Abstract: PREPARATION AND PROPERTIES OF CYCLOBUTANETHIONES

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