82494-85-7Relevant academic research and scientific papers
Organic syntheses via transition metal complexes, CV: Regiocontrol of annelation of cyclopentene-1-thiones and cyclopenten-1-ones to alkenes with the aid of (1-alkynyl)carbene complexes (M = Cr, W)
Wu, He-Ping,Aumann, Rudolf,Venne-Dunker, Sabine,Saarenketo, Pauli
, p. 3463 - 3473 (2000)
Bicyclic olefins containing a 1-oxy-3-thiocyclopentadiene unit were obtained with high regioselectivity from [2-(cyclo-alk-1-enyl)-1-alkynyl]carbene complexes 1a-d and thiols 2a-c under mild conditions. If the reaction was performed in a protic solvent like ethanol, the produced allylthiocyclopentadienes 5 spontaneously underwent a thio Claisen rearrangement to give cyclopentene-1-thione complexes 3 in 62-72% yields. In nonprotic solvents, additional cyclopentene-1-thione complexes 6 and 7 were obtained as a result of the incorporation of two and three allylthiol units, respectively. Arylthiotetrahydroindene complexes 12b and c could be isolated in 76-79% yields. The corresponding tetrahydropentalene derivative 12a was unstable, but could be trapped by [2+2] cycloaddition of (1-alkynyl)carbene complex 1a to give a stable (cyclobutenyl)carbene complex 15. Hydrolysis of compounds 12a-c afforded cyclopenten-1-ones 13a-c.
Silicon in Synthesis. 21. Reagents for Thiophenyl-Functionalized Cyclopentenone Annulations and the Total Synthesis of (+/-)-Hirsutene
Magnus, Philip,Quagliato, Dominick
, p. 1621 - 1626 (2007/10/02)
1-(Trimethylsilyl)-1-(phenylthio)ethylene (1) reacts with cyclic α,β-unsaturated acid chlorides to give β-mercaptophenyl-substituted cyclopentenones, whereas 1-(trimethylsilyl)-2-(phenylthio)ethylene (2) under similar conditions results in thiophenyl migr
Silicon in Synthesis. 8. Vinyltrimethylsilane, a Convenient Ethylene Equivalent for the Synthesis of Vinyl Aryl Sulfides, Vinyl Aryl Sulfoxides, Thiosilylketene Acetals, and Fused Cyclopentenones
Cooke, Frank,Moerck, Rudi,Schwindeman, James,Magnus, Phillip
, p. 1046 - 1053 (2007/10/02)
Vinyltrimethylsilane reacts with a variety of arylsulfenyl chlorides to give 2-chloro-1-(trimethylsilyl)ethyl aryl sulfide adducts 9-13.These adducts can be converted into vinyl aryl sulfides and vinyl aryl sulfoxides, and for the case of 2-chloro-1-(trimethylsilyl)ethyl phenyl sulfide (11), treatment with 1,5-diazabicyclonon-5-ene (DBN) gave 1-(trimethylsilyl)-1-(phenylthio)ethylene (24). α,β-Unsaturated acid chlorides react with vinyltrimethylsilane in the presence of stannic tetrachloride to give fused cyclopentenones.In all of the reaction described, vinyltrimethylsilane serves as a convenient ethylene equivalent.
