“…Isolated as a pale yellow oil (69.8 mg, 61%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.33−7.25 (m, 2H), 6.73−6.64 (m, 2H), 4.75 (s, 1H), 2.95 (s, 6H), 2.09 (s, 6H). 13 ((4-Phenoxyphenyl)methylene)bis(methylsulfane) (11b).…”
Section: ■ Conclusionmentioning
confidence: 99%
“…Isolated as a brown oil (165.0 mg, 92%). 1 3-Bromo-4-((4-(dimethylamino)phenyl)(phenyl)methyl)-N,N-dimethylaniline (1g). Synthesized according to procedure C with 3-bromo-N,N-dimethylaniline as a nucleophile.…”
“…Flash column chromatography was performed on silica gel 60 (40−63 μm). 1 H and 13 C spectra were recorded at 400 and 100 MHz, respectively. The chemical shifts for 1 H NMR and 13 C NMR are referenced to Tetramethylsilane via residual solvent signals (1H: CDCl 3 at 7.26 ppm and DMSO-d 6 at 2.50 ppm; 13 C: CDCl 3 at 77.16 ppm and DMSO-d 6 at 39.52 ppm).…”
Section: ■ Conclusionmentioning
confidence: 99%
“…Purified over silica using 5% EtOAc in i-hexane. Isolated as a white solid (114.0 mg, 89%) 1. H NMR (400 MHz, CDCl 3 ) δ 7.47−7.40 (m, 2H), 7.36−7.25 (m, 4H), .…”
Herein, a method
for thioacetalation using BF3SMe2 is presented.
The method allows for convenient and odor-free
transformation of aldehydes to methyl-dithioacetals, a simple but
sparsely reported structural moiety, in good yields with a diverse
set of aromatic aldehydes. In addition, a thiomethylative Friedel-Crafts
reaction was discovered, affording thiomethylated diarylmethanes in
good to excellent yields. The resulting diarylmethane core is of interest
as it is found in many biologically active compounds, and its utility
is further demonstrated as a novel precursor to unsymmetrical triarylmethanes.
This work also highlights the usefulness and the synthetic capabilities
of the readily available reagent BF3SMe2 beyond
its reactivity profile as a dealkylation reagent.
“…Isolated as a pale yellow oil (69.8 mg, 61%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.33−7.25 (m, 2H), 6.73−6.64 (m, 2H), 4.75 (s, 1H), 2.95 (s, 6H), 2.09 (s, 6H). 13 ((4-Phenoxyphenyl)methylene)bis(methylsulfane) (11b).…”
Section: ■ Conclusionmentioning
confidence: 99%
“…Isolated as a brown oil (165.0 mg, 92%). 1 3-Bromo-4-((4-(dimethylamino)phenyl)(phenyl)methyl)-N,N-dimethylaniline (1g). Synthesized according to procedure C with 3-bromo-N,N-dimethylaniline as a nucleophile.…”
“…Flash column chromatography was performed on silica gel 60 (40−63 μm). 1 H and 13 C spectra were recorded at 400 and 100 MHz, respectively. The chemical shifts for 1 H NMR and 13 C NMR are referenced to Tetramethylsilane via residual solvent signals (1H: CDCl 3 at 7.26 ppm and DMSO-d 6 at 2.50 ppm; 13 C: CDCl 3 at 77.16 ppm and DMSO-d 6 at 39.52 ppm).…”
Section: ■ Conclusionmentioning
confidence: 99%
“…Purified over silica using 5% EtOAc in i-hexane. Isolated as a white solid (114.0 mg, 89%) 1. H NMR (400 MHz, CDCl 3 ) δ 7.47−7.40 (m, 2H), 7.36−7.25 (m, 4H), .…”
Herein, a method
for thioacetalation using BF3SMe2 is presented.
The method allows for convenient and odor-free
transformation of aldehydes to methyl-dithioacetals, a simple but
sparsely reported structural moiety, in good yields with a diverse
set of aromatic aldehydes. In addition, a thiomethylative Friedel-Crafts
reaction was discovered, affording thiomethylated diarylmethanes in
good to excellent yields. The resulting diarylmethane core is of interest
as it is found in many biologically active compounds, and its utility
is further demonstrated as a novel precursor to unsymmetrical triarylmethanes.
This work also highlights the usefulness and the synthetic capabilities
of the readily available reagent BF3SMe2 beyond
its reactivity profile as a dealkylation reagent.
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