35905-68-1

Upstream product

• 163979-79-1 Acetic acid ethylsulfanyl-phenyl-methyl ester 
• 762-72-1 allyl-trimethyl-silane 
• 169172-96-7 α-Methoxy-α-(ethylthio)toluene 
• 24850-33-7 allyltributylstanane 
• 59340-48-6 <α-(ethylthio)benzyloxy>trimethylsilane 
• 7334-52-3 benzaldehyde diethyldithioacetal 

Relevant academic research and scientific papers

The synthesis of α-acetoxy sulfides and their Lewis acid-mediated reactions

α-Acetoxy sulfides can be conveniently prepared by the reaction of dithioacetals with mercuric acetate at ambient temperature. They react with allyltrimethylsilane, enol silyl ethers, and cyanotrimethylsilane in the presence of SnCl4 to afford

Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane

On the basis of preferential complexation of oxygen or selenium atoms by different Lewis acids, it was expected that, depending on the Lewis acid employed, the title reactions would lead to selective formation of homoallyl ethers or homoallyl selenides.This has not been confirmed by experiment: in almost all the reactions tried homoallyl ethers largely predominated, or were the exclusive allylation products, even when strongly oxygenophilic Lewis acids such as TiCl4 were used.In the cases of the latter type of Lewis acids, the results observed with (O,Se) and a couple of (O, S) mixed acetals are interpreted in terms of two major factors operating in opposite directions. 1H NMR data of a mixture of TiCl4 and (O,Se) acetal indicate that preferential (but not exclusive) complexation of the oxygen moiety takes place indeed.However, because of the much stronger C-O bond as compared to the C-Se bond, this latter (also activated by the Lewis acid to some extent) undergoes cleavage by allyl metals to give homoallyl ethers as predominating products.In contrast with BF3*OEt2, boron trichloride and boron tribromide were found to react with (O, Se) acetals to give the corresponding α-halo selenides, which in turn were cleanly transformed into homoallyl selenides on reaction with allyltrimethylsilane in the presence of tin tetrachloride.

An Effective Activation of O-Trimethylsilyl Monothioacetal under Extremely Mild Conditions Using a Novel Catalyst System, Trimethylsilyl Chloride and Indium(III) Chloride

A novel catalyst system, trimethylsilyl chloride and indium(III) chloride, effectively catalyzes the reaction of O-trimethylsilyl monothioacetals with triethylsilane and silylated carbon nucleophiles, respectively, to afford the corresponding sulfide derivatives in good to high yields.

Gallium Chloride-Mediated Allylation of Dithioacetals with Allylstannanes

In the presence of gallium chloride, dithioacetals reacted with allylstannanes to give the corresponding homoallyl sulfides in high yields.The present method could be applied to the chemoselective allylation of bis(dithioacetal) of keto aldehyde, and the