7695-69-4Relevant 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.
Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes
Vale, Joao R.,Rimpil?inen, Tatu,Siev?nen, Elina,Rissanen, Kari,Afonso, Carlos A. M.,Candeias, Nuno R.
, p. 1948 - 1958 (2018/02/23)
The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
Cyanuric chloride-catalyzed thioacetalization for organocatalytic synthesis of thioacetals
Liu, Yaqin
, p. 679 - 682 (2016/05/09)
The thioacetalization of aromatic aldehydes has been realized with broad diversity in the presence of various thiols and thiophenols using cyanuric chloride as an organocatalyst.
