2-Phenylthio-3,3,3-trifluoropropene, its sulfoxide and sulfone: Synthesis and reactivity in 1,3-dipolar cycloadditions

1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes

“…Once the 13 C NMR spectra had indicated decomposition, the 1 H NMR spectra were re-recorded and comparison of both the 1 H and 13 C NMR spectroscopic data with those of pure samples of 61 and 58 (which had been previously synthesised independently) confirmed the identity of these decomposition products. Thus, while the sulfinyl pyrazolines were stable as solids and in CDCl 3 , they undergo spontaneous elimination in DMSO-d 6 .…”

“…The 1 H NMR spectra of the crude products were very complex and the isolated yields were poor (16-40%); some decomposition may have occurred during chromatography on the silica gel. While the 13 C NMR spectra of the pyrazolines 66 and 67 could be recorded in CDCl 3 , with the less stable pyrazolines 68 and 69 the 13 C NMR spectra were recorded in DMSO-d 6 , and analysis of the spectra indicated that the pyrazolines had decomposed to the corresponding pyrazoles 61 and 58 on dissolution in DMSO-d 6 (Scheme 9). Once the 13 C NMR spectra had indicated decomposition, the 1 H NMR spectra were re-recorded and comparison of both the 1 H and 13 C NMR spectroscopic data with those of pure samples of 61 and 58 (which had been previously synthesised independently) confirmed the identity of these decomposition products.…”

“…5,6 A series of reports over the past 15 years from Garcia Ruano's group discuss in detail 1,3-dipolar cycloadditions of diazomethane and diazoethane to vinyl sulfoxides of direct relevance to this work. [7][8][9][10][11][12] However, the presence of the 3-chloro substituent in the dipolarophiles in the current work potentially has a significant electronic effect on their reactivity, and more importantly, leads to chloro-substituted heterocycles, where the presence of the chloride substituent offers considerable synthetic potential and diversity via substitution and coupling processes.…”

Characterization of Palladium Chelates and Their Interactions with Z-N'-(Benzo(d)Thiazol-2-yl)-N,N-Dimethylformimidamide using the Spectrophotometric and Computational Methods

“…Only few studies in the literature have been demonstrated the utilize of pyrazolyl derivative complexes for assembly or self-assembly in extended arrays 15 . Some derivatives of five-membered heterocycles have subjected to considerable attention in the literature 16 , in particular, studies on the synthesis of trifluoromethylsubstituted isoxazoles and pyrazoles [17][18][19] . In this work, the interactions of Z-N'-(benzo(d)thiazol-2-yl)-N,N-dimethylformimidamide ligand with Pd(II) were investigated experimentally for the first time using a simple, easy to operate, reliable, highly sensitive and accurate extractive spectrophotometric method for the detection and quantification of Pd(II) in spiking different water samples and these interactions were approved using quantum chemical calculations by calculating the HOMO/LUMO energy values and bond angles, bond lengths, charge density and dihedral angles of the complexes.…”

Enantiomerically Pure trans-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides

“…Ylide equivalents containing heteroatoms such as nitrogen or sulfur 2 are useful intermediates for the addition to dipolarophiles such as α,β-unsaturated acyl derivatives. Such 1,3-dipolar cycloaddition reactions can result in the formation of five-membered rings (for example, pyrrolidine or tetrahydrothiophene derivatives) in one single step.…”