20912-85-0Relevant articles and documents
Laser flash photolysis study of dialkylphenacylsulfonium salts
Kawamura, Koichi,Kodama, Kunihiko,Hirai, Katsuyuki,Tomioka, Hideo
, p. 148 - 149 (2004)
Laser flash photolysis of the title compound in degassed acetonitrile at room temperature revealed the presence of transient species showing the absorption at 480 nm, regardless of the structure of the precursors. The transient bands are assigned to phenacyl radical presumably formed as a result of the carbon-sulfur bond rather than 1,4-biradicals or cationic species proposed to be formed as a result of Norrish Type II process.
Chlorotrifluoromethylthiolation of Sulfur Ylides for the Formation of Tetrasubstituted Trifluoromethylthiolated Alkenes
Wang, Na,Jia, Yimin,Qin, Hongmei,Jiang, Zhong-Xing,Yang, Zhigang
, p. 7378 - 7382 (2020/10/05)
Tetrasubstituted trifluoromethylthiolated alkenes can be accomplished directly through the chlorotrifluoromethylthiolation of sulfur ylides utilizing nucleophilic halide reagent and electrophilic SCF3 reagent. This cascade reaction is mild, highly practical, easy to manipulate, uses catalyst-free conditions, and demonstrates a wide substrate range with excellent functional group tolerance, furnishing E-selective products in good to high yields. The synthetic utility of this approach is documented through gram-scale preparation and late-stage modification of pharmaceutically relevant compounds, making it suitable for drug discovery.
Base Catalysed Rearrangements Involving Ylide Intermediates. Part 9. The Rearrangement Reactions of Cyclic Allylic Ammonium and Sulphonium Ylides
Mageswaran, Sivapathasuntharam,Ollis, W. David,Sutherland, Ian O.
, p. 1953 - 1962 (2007/10/02)
The allylic ammonium ylides (22) and (47) and sulphonium ylide (53) are isolable, usually as crystalline solids, because their sigmatropic rearrangements are inhibited by the strain associated with the bicyclic transition state of a concerted reaction mechanism.The tetrahydropyridinium (22) and dihydrothiopyranium (29) ylides undergo a thermal rearrangement, but the pyrrolinium ylide (47) rearranges by a , rather than a , sigmatropic pathway.The dihydrothiophenium ylide (53) does not undergo either a or sigmatropic rearrangement but instead reacts in a bimolecular fashion to give eventually buta-1,3-diene, 2,5-dihydrothiophen, and the heterocycle (55).The rearrangements of the ylides (22) and (29) follow predominantly an endo-pathway leading to a single diastereomer of the products (23) and (31); this strong endo preference is not shown by analogous acyclic ammonium ylides.
Reactions of group IV organometallic compounds XXV. Preparations and reactions of tetramethylene-[(α-trimethylsilyl- or α-trimethylstannyl)phenacyl]sulphonium salts and ylides
Itoh, Kenji,Kato,Ishii
, p. 293 - 298 (2007/10/10)
Tetramethylene[(α-trimethylsilyl- and α-trimethylstannyl)phenacyl]sulphonium salts [(CH2)4S+CH(MMe3)COPh]Cl- (M = Si and Sn) have been prepared by the reaction of tetramethylenesulphonium phenacyclide (I) with the relevant Me3MCl. The thermal rearrangement of tetramethylene[(α-trimethylsilyl)phenacyl]sulphonium chloride (II) unexpectedly afforded Cl(CH2)4SCHC(OSiMe3)Ph (III) by a 1,3-migration of the trimethylsilyl group to the oxygen atom accompanied by simultaneous ring-opening. Tetramethylene[(α-trimethylstannyl)phenacyl]sulphonium chloride (IV) gave the corresponding ylide (VI) by reaction with n-butyllithium.
