- Direct Synthesis of Unsymmetrical Dithioacetals
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Dithioacetals are a frequently used motif in synthetic organic chemistry and have recently seen increasing attention as structural motif in promising antiviral agents against plant pathogens. Most existing reports, however, only discuss symmetrical dithioacetals. Examples of mixed dithioacetals are scarce and no general method for the selective synthesis of these compounds exists. Herein, a synthetically simple general one-step protocol was developed for the synthesis of a broad range of unsymmetrical dithioacetals consisting of one aromatic and one aliphatic thiol moiety from the corresponding aldehyde/thiol mixture. The mixed S,S-acetals were obtained in high yields, and a great variety of functional groups was tolerated. Kinetic control enabled an excellent selectivity in regard to the unsymmetrical dithioacetal.
- Bognar, Sabine,van Gemmeren, Manuel
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supporting information
p. 4859 - 4863
(2021/02/03)
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- Thioacetalization of aldehydes and ketones in SDS micelles
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Aromatic aldehydes have been successfully converted into their corresponding dithioacetal, dithiolane and dithiane derivatives in excellent yields with thiol (benzyl thiol and thiophenol), 1,2-ethanedithiol and 1,3-propanedithiol using trichloroacetic acid in sodium dodecyl sulfate micelles. The same procedure is applicable to ketones, but they need more time to be converted into their thioacetals. Image Presented.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Tajik, Maryam,Soheilizad, Mehdi
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experimental part
p. 397 - 403
(2012/06/18)
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- Silica-supported phosphorus pentoxide: A reusable catalyst for S,S-acetalization of carbonyl groups under ambient conditions
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Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) efficiently acts as a highly active and reusable catalyst for cyclic and non-cyclic S,S-acetalization of a variety of carbonyl compounds under mild, solvent-free an
- Shaterian, Hamid Reza,Azizi, Kobra,Fahimi, Nafiseh
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experimental part
p. 85 - 91
(2012/01/06)
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- TETRACHLOROSILANE CATALYZED DITHIOACETALIZATION
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Tetrachlorosilane was found to be a mild as well as selective catalyst for dithioacetalization of the carbonyl compounds.
- Ku, Bonchul,Oh, Dong Young
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p. 433 - 438
(2007/10/02)
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