Carbonyl-Stabilized Sulfonium Ylids. Reaction with Schiff Bases

Speziale, A. J.; Tung, C. C.; Ratts, K. W.; Yao, A. N.

doi:10.1021/ja01093a031

Cited by 60 publications

(7 citation statements)

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“…However, the intermediate 5 could form the ester 2 in several ways. One possible pathway is via an aziridine 6 (Scheme 2, path a) as suggested (4) by analogy with the known formation of aziridines from imines and sulfur ylids (5). Nevertheless, we consider that another pathway, involving a p-elimination, is more likely, especially for the formation of unsaturated esters of type 2 (Scheme 2, path b).…”

Section: Resultsmentioning

confidence: 88%

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The conversions of isothiazolium salts into thiophenecarboxylic ester derivatives

McKinnon¹,

Duncan²,

Millar³

1984

Can. J. Chem.

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Several 3-aminothiophene-2-carboxylic ester derivatives are made by reaction of potassium 3-ethoxy-3-oxopropanoate with isothiazolium salts or by reaction with 2-ethoxy-2-oxoethylidenedimethylsulfurane. In the latter case deaminated products are also isolated. These products are consistent with initial nucleophilic attack on the sulfur atom of the isothiazolium salt. In one case a pyrrole derivative is formed by a novel rearrangement of an intermediate aziridine derivative. Some further derivatives of 3-benzylaminobenzo[b]thiophene are described.

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Section: Resultsmentioning

confidence: 88%

“…3.5-3.8 (two 4H, m, the pyrrolidinyl), 4 Attempted thionation of 10c in benzenc with phosphorus penSpectra. tasulfide gave only a small amount of a complex yellow oil on work-UP.…”

mentioning

confidence: 99%

The conversions of isothiazolium salts into thiophenecarboxylic ester derivatives

McKinnon¹,

Duncan²,

Millar³

1984

Can. J. Chem.

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“…Identification of 4 and 5 was possible on the basis of comparison of their NMR data with similar compounds …”

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confidence: 99%

Lewis Acid-Catalyzed Synthesis of Aziridines

et al. 1996

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“…t ‐Butyl(dimethylsulfuranylidene)acetate was prepared according to the method described previously29; 220 mg (1.25 m M ) of the above mentioned yield was dissolved in 50 ml of toluene and added to 500 mg (0.69 mmol) C60 dissolved in 500‐ml toluene. The mixture was stirred at room temperature for 8 h. The product consisting of mono‐, di‐ and tri‐adduct was separated by flash column chromatography using silica gel 60, and toluene as mobile phase.…”

Section: Methodsmentioning

confidence: 99%

Laser desorption/ionization mass spectrometric analysis of small molecules using fullerene‐derivatized silica as energy‐absorbing material

et al. 2010

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In spite of the growing acceptance of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for the analysis of a wide variety of compounds, including polymers and proteins, its use in analyzing low-molecular-weight molecules (<1000 m/z) is still limited. This is mainly due to the interference of matrix molecules in the low-mass range. Here the derivatized fullerenes covalently bound to silica particles with different pore sizes are applied as thin layer for laser desorption/ionization (LDI) mass spectrometric analysis. Thus, an interference of intrinsic matrix ions can be eliminated or minimized in comparison with the state-of-the-art weak organic acid matrices. The desorption/ionization ability of the developed fullerene-silica materials depends on the applied laser power, sample preparation and pore size of the silica particles. Thus, fullerene-silica serves as an LDI support for mass spectrometric analysis of molecules (<1500 Da). The performance of the fullerene-silica is demonstrated by the mass analysis of variety of small molecules such as carbohydrates, amino acids, peptides, phospholipids and drugs.

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Carbonyl-Stabilized Sulfonium Ylids. Reaction with Schiff Bases

Cited by 60 publications

References 0 publications

The conversions of isothiazolium salts into thiophenecarboxylic ester derivatives

The conversions of isothiazolium salts into thiophenecarboxylic ester derivatives

Lewis Acid-Catalyzed Synthesis of Aziridines

Laser desorption/ionization mass spectrometric analysis of small molecules using fullerene‐derivatized silica as energy‐absorbing material

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