25850-55-9Relevant articles and documents
Direct Synthesis of Unsymmetrical Dithioacetals
Bognar, Sabine,van Gemmeren, Manuel
supporting information, p. 4859 - 4863 (2021/02/03)
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.
A Transition-Metal-Free and Base-Mediated Carbene Insertion into Sulfur-Sulfur and Selenium-Selenium Bonds: An Easy Access to Thio- and Selenoacetals
Arunprasath, Dhanarajan,Sekar, Govindasamy
, p. 698 - 708 (2017/02/23)
A transition-metal-free and base-mediated carbene insertion across sulfur-sulfur and selenium-selenium bonds has been developed by employing N-tosylhydrazone as a stable and safe carbene precursor. The ylide formation from carbene followed by Stevens rearrangement are considered to be the key steps. This thiol and selenol-free protocol delivers thioacetals and selenoacetals in good to excellent yields in short reaction time with good functional group tolerance. A one-pot synthesis involving in situ generation of tosylhydrazone has also been demonstrated. (Figure presented.).
Green, catalyst-free thioacetalization of carbonyl compounds using glycerol as recyclable solvent
Perin, Gelson,Mello, Luzia G.,Radatz, Cátia S.,Savegnago, Lucielli,Alves, Diego,Jacob, Raquel G.,Lenard?o, Eder J.
experimental part, p. 4354 - 4356 (2010/09/12)
We describe herein the use of glycerol as an efficient and a recyclable solvent in the thioacetalization of aldehydes and ketones. The catalyst-free reactions proceed easily using glycerol at 90 °C and the corresponding thioacetals were obtained in good to excellent yields. Glycerol was recovered and utilized for further thioacetalization reactions.
