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Heimgartner Heinz - One of the best experts on this subject based on the ideXlab platform.

  • Studies on Reactions of Thioketones with Trimethyl(trifluoromethyl)silane Catalyzed by Fluoride Ions
    Wiley-Blackwell Publishing Inc., 2002
    Co-Authors: Mlostoń Grzegorz, Prakash G K Surya, Olah, George A, Heimgartner Heinz
    Abstract:

    Treatment of 2,2,4,4-tetramethylcyclobutane-1,3-dione (6) in THF with CF3SiMe3 in the presence of tetrabutylammonium fluoride (TBAF) yielded the corresponding 3-(trifluoromethyl)-3-[(trimethylsilyl)oxy]cyclobutanone 7 (Scheme 1) via nucleophilic addition of a CF3 anion at the C=O group and subsequent silylation of the alcoholate. Under similar conditions, the 'monothione' 1 reacted to give Thietane Derivative 8 (Scheme 2), whereas in the case of 'dithione' 2 only the dispirodiThietane 9, the dimer of 2, was formed (Scheme 3). A conceivable mechanism for the formation of 8 is the ring opening of the primarily formed CF3 adduct A followed by ring closure via the S-atom (Scheme 2). In the case of thiobenzophenones 4, complex mixtures of products were obtained including diarylmethyl trifluoromethyl sulfide 10 and 1,1-diaryl-2,2-difluoroethene 11 (Scheme 4). Obviously, competing thiophilic and carbophilic addition of the CF3 anion took place. The reaction with 9H-fluorene-9-thione (5) yielded only 9,9'-bifluorenylidene (14; Scheme 6); this product was also formed when 5 was treated with TBAF alone. Treatment of 4a with TBAF in THF gave dibenzhydryl disulfide (15; Scheme 7), whereas, under similar conditions, 1 yielded the 3-oxopentanedithioate 17 (Scheme 9). The reaction of dithione 2 with TBAF led to the isomeric dithiolactone 16 (Scheme 8), and 3 was transformed into 1,2,4-trithiolane 18 (Scheme 10)

Mlostoń Grzegorz - One of the best experts on this subject based on the ideXlab platform.

  • Studies on Reactions of Thioketones with Trimethyl(trifluoromethyl)silane Catalyzed by Fluoride Ions
    Wiley-Blackwell Publishing Inc., 2002
    Co-Authors: Mlostoń Grzegorz, Prakash G K Surya, Olah, George A, Heimgartner Heinz
    Abstract:

    Treatment of 2,2,4,4-tetramethylcyclobutane-1,3-dione (6) in THF with CF3SiMe3 in the presence of tetrabutylammonium fluoride (TBAF) yielded the corresponding 3-(trifluoromethyl)-3-[(trimethylsilyl)oxy]cyclobutanone 7 (Scheme 1) via nucleophilic addition of a CF3 anion at the C=O group and subsequent silylation of the alcoholate. Under similar conditions, the 'monothione' 1 reacted to give Thietane Derivative 8 (Scheme 2), whereas in the case of 'dithione' 2 only the dispirodiThietane 9, the dimer of 2, was formed (Scheme 3). A conceivable mechanism for the formation of 8 is the ring opening of the primarily formed CF3 adduct A followed by ring closure via the S-atom (Scheme 2). In the case of thiobenzophenones 4, complex mixtures of products were obtained including diarylmethyl trifluoromethyl sulfide 10 and 1,1-diaryl-2,2-difluoroethene 11 (Scheme 4). Obviously, competing thiophilic and carbophilic addition of the CF3 anion took place. The reaction with 9H-fluorene-9-thione (5) yielded only 9,9'-bifluorenylidene (14; Scheme 6); this product was also formed when 5 was treated with TBAF alone. Treatment of 4a with TBAF in THF gave dibenzhydryl disulfide (15; Scheme 7), whereas, under similar conditions, 1 yielded the 3-oxopentanedithioate 17 (Scheme 9). The reaction of dithione 2 with TBAF led to the isomeric dithiolactone 16 (Scheme 8), and 3 was transformed into 1,2,4-trithiolane 18 (Scheme 10)

Prakash G K Surya - One of the best experts on this subject based on the ideXlab platform.

  • Studies on Reactions of Thioketones with Trimethyl(trifluoromethyl)silane Catalyzed by Fluoride Ions
    Wiley-Blackwell Publishing Inc., 2002
    Co-Authors: Mlostoń Grzegorz, Prakash G K Surya, Olah, George A, Heimgartner Heinz
    Abstract:

    Treatment of 2,2,4,4-tetramethylcyclobutane-1,3-dione (6) in THF with CF3SiMe3 in the presence of tetrabutylammonium fluoride (TBAF) yielded the corresponding 3-(trifluoromethyl)-3-[(trimethylsilyl)oxy]cyclobutanone 7 (Scheme 1) via nucleophilic addition of a CF3 anion at the C=O group and subsequent silylation of the alcoholate. Under similar conditions, the 'monothione' 1 reacted to give Thietane Derivative 8 (Scheme 2), whereas in the case of 'dithione' 2 only the dispirodiThietane 9, the dimer of 2, was formed (Scheme 3). A conceivable mechanism for the formation of 8 is the ring opening of the primarily formed CF3 adduct A followed by ring closure via the S-atom (Scheme 2). In the case of thiobenzophenones 4, complex mixtures of products were obtained including diarylmethyl trifluoromethyl sulfide 10 and 1,1-diaryl-2,2-difluoroethene 11 (Scheme 4). Obviously, competing thiophilic and carbophilic addition of the CF3 anion took place. The reaction with 9H-fluorene-9-thione (5) yielded only 9,9'-bifluorenylidene (14; Scheme 6); this product was also formed when 5 was treated with TBAF alone. Treatment of 4a with TBAF in THF gave dibenzhydryl disulfide (15; Scheme 7), whereas, under similar conditions, 1 yielded the 3-oxopentanedithioate 17 (Scheme 9). The reaction of dithione 2 with TBAF led to the isomeric dithiolactone 16 (Scheme 8), and 3 was transformed into 1,2,4-trithiolane 18 (Scheme 10)

Olah, George A - One of the best experts on this subject based on the ideXlab platform.

  • Studies on Reactions of Thioketones with Trimethyl(trifluoromethyl)silane Catalyzed by Fluoride Ions
    Wiley-Blackwell Publishing Inc., 2002
    Co-Authors: Mlostoń Grzegorz, Prakash G K Surya, Olah, George A, Heimgartner Heinz
    Abstract:

    Treatment of 2,2,4,4-tetramethylcyclobutane-1,3-dione (6) in THF with CF3SiMe3 in the presence of tetrabutylammonium fluoride (TBAF) yielded the corresponding 3-(trifluoromethyl)-3-[(trimethylsilyl)oxy]cyclobutanone 7 (Scheme 1) via nucleophilic addition of a CF3 anion at the C=O group and subsequent silylation of the alcoholate. Under similar conditions, the 'monothione' 1 reacted to give Thietane Derivative 8 (Scheme 2), whereas in the case of 'dithione' 2 only the dispirodiThietane 9, the dimer of 2, was formed (Scheme 3). A conceivable mechanism for the formation of 8 is the ring opening of the primarily formed CF3 adduct A followed by ring closure via the S-atom (Scheme 2). In the case of thiobenzophenones 4, complex mixtures of products were obtained including diarylmethyl trifluoromethyl sulfide 10 and 1,1-diaryl-2,2-difluoroethene 11 (Scheme 4). Obviously, competing thiophilic and carbophilic addition of the CF3 anion took place. The reaction with 9H-fluorene-9-thione (5) yielded only 9,9'-bifluorenylidene (14; Scheme 6); this product was also formed when 5 was treated with TBAF alone. Treatment of 4a with TBAF in THF gave dibenzhydryl disulfide (15; Scheme 7), whereas, under similar conditions, 1 yielded the 3-oxopentanedithioate 17 (Scheme 9). The reaction of dithione 2 with TBAF led to the isomeric dithiolactone 16 (Scheme 8), and 3 was transformed into 1,2,4-trithiolane 18 (Scheme 10)