143885-01-2Relevant articles and documents
A new method for the preparation of fluoro-λ6-sulfanenitriles: Reaction of sulfimides with Selectfluor
Fujii, Takayoshi,Asai, Shinsuke,Okada, Tomoyuki,Hao, Wei,Morita, Hiroyuki,Yoshimura, Toshiaki
, p. 6203 - 6205 (2007/10/03)
Several diaryl(fluoro)-λ6-sulfanenitriles 3 were synthesized by the reaction of S,S-diarylsulfimides 1 with Selectfluor. This reaction also allows the first preparation of heterocyclic fluoro-λ6-sulfanenitrile, 5-fluoro-10,10-dioxo-5,10-dihydro-5λ6,10λ 6-thianthren-5-nitrile (5) and its molecular structure was determined by X-ray crystallographic analysis.
Synthesis, Structure, and Thermolysis Mechanism of S-Alkoxythiazynes
Yoshimura, Toshiaki,Ohkubo, Masanori,Fujii, Takayoshi,Kita, Hiroshi,Wakai, Youko,Ono, Shin,Morita, Hiroyuki,Shimasaki, Choichiro,Horn, Ernst
, p. 1629 - 1637 (2007/10/03)
S-Alkoxy-S,S-diarylthiazynes were prepared by two methods: the alkaline hydrolysis of S,S-diaryl-N-halosulfilimines in aqueous alcohols and the reaction of S,S-diaryl-S-fluorothiazynes with sodium alkoxides. The structure of S,S-diphenyl-S-propoxythiazyne was determined by an X-ray crystallographic analysis, which showed a short SN bond length of 1.441(3) A. The thermolysis of S-alkoxythiazynes gave elimination products, which were identified as the corresponding carbonyl compounds and N-unsubstituted S,S-diarylsulfilimines. Kinetic experiments for the thermolysis of the S-alkoxy-S,S-diarylthiazynes were carried out. The first-order kinetic behavior, a large kinetic isotope effect (kHkD = 6.1 ) using S,S-diphenyl-S-[1,1-2H2]propoxythiazyne, a negative activation entropy (ΔS? = -30 J K-1mol-1), and a negative Hammett ρ-value (ρ= -0.35) on the phenyl group were obtained, suggesting that the reaction proceeds via a concerted five-membered cyclic transition state. A deviation from the ideal concerted transition state is discussed in comparison with that for sulfoxides.
First Preparation and Reactions of S,S-Diaryl-S-fluorothiazynes, Ar2SF(N)
Yoshimura, Toshiaki,Kita, Hiroshi,Takeuchi, Kyu,Takata, Eiichi,Hasegawa, Kiyoshi,et al.
, p. 1433 - 1436 (2007/10/02)
S,S-Diaryl-S-fluorothiazynes, Ar2SF(N), were prepared by the reaction of S,S-diaryl-N-bromosulfilimines with tetrabutylammonium fluoride.The thiazyne structure was assigned by the spectral data, physical properties, and is consistent with reactions wit