94158-05-1Relevant articles and documents
Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum
Kita, Masaki,Watanabe, Masami,Takada, Noboru,Suenaga, Kiyotake,Yamada, Kaoru,Uemura, Daisuke
, p. 6405 - 6412 (2002)
Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.
Synthesis of Novel Cyclic Sulfone Dihydropyridines Facilitated by a Selective Ethyl Diazoacetate Ring Expansion
Dodd, John H.,Schwender, Charles F.,Gray-Nunez, Yolanda
, p. 1453 - 1456 (2007/10/02)
A series of novel cyclic sulfone dihydropyridines with five to nine membered rings have been synthesized.Anomalous intermediates isolated from the Hantzch condensation were found to vary depending on the sulfone ring size and aromatic substitution.Tin tetrachloride has been shown to be a superior Lewis acid catalyst for ethyl diazoacetate ring expansion of the requisite β-keto cyclic sulfone precursors.
Conformational Analysis. 46. Conformational Equilibria in 3-Hydroxy-, 3-Methoxy-, and 3-Acetoxythianes, Their Sulfoxides and Sulfones, and Some Corresponding 3-Methyl Homologues
Brunet, Ernesto,Eliel, Ernest L.
, p. 677 - 686 (2007/10/02)
Conformational equilibria have been measured, by low-temperature carbon-13 and proton NMR spectroscopy, for 3-hydroxythiane, its two epimeric sulfoxides, and the corresponding sulfone and their methyl ethers and acetates, as well as the corresponding derivatives of 3-methyl-3-hydroxythiane and their acetates.Of particular note are large solvent and concentration effects on the conformational free energies, ΔG0ae, especially in cases where intramolecular and intermolecular hydrogen bonding are competitive.Thus, in 3-hydroxythiane, ΔG0 rises from -1.20 kcal/mol in 4 M CD2Cl2 to -0.22 kcal/mol in 0.0011 M CD2Cl2; for the corresponding cis sulfoxide the rise is from +1.3 kcal/mol in 0.0023 M CD2Cl2 and in the sulfone it is from -1.3 kcal/mol in 0.3 M CD3COCD3 to -0.9 kcal/mol in 0.3 M CD2Cl2 to -0.16 kcal/mol in 0.002 M CD2Cl2.
