19844-05-4Relevant academic research and scientific papers
THIOL ESTER IN ORGANIC SYNTHESIS XV. REDUCTION WITH TETRABUTYLAMMONIUM BOROHYDRIDE
Liu, Hsing-Jang,Luo, Weide
, p. 387 - 392 (2007/10/02)
Treatment of thiol ester with tetrabutylammmonium borohydride in refluxing chloroform gave rise to the corresponding alcohols.
REACTION OF THIOACETALS WITH TRIETHYLSILANE IN THE PRESENCE OF LEWIS ACIDS AND REDUCED NICKEL
Kirilyuk, B. A.,Mel'nitskii, I. A.,Golub, N. M.,Kiladze, T. K.,Kantor, E. A.,Rakhmankulov, D. L.
, p. 1754 - 1758 (2007/10/02)
1,1-Di(alkylthio)alkanes, 1,3-oxathiolanes, 1,3-dithiolanes, and ortho thioesters are cleaved by triethylsilane in the presence of catalytic amounts of zinc iodide or reduced nickel.In the presence of zinc iodide the acyclic dithioacetals and ortho thioester are converted into alkyl sulfides and triethyl(alkylthio)silanes by cleavage of the carbon-sulfur bond.The analogs of the cyclic acetals are cleaved by triethylsilane only in the presence of reduced nickel, while regiospecific cleavage of the heterocycle at the carbon-oxygen bond is observed in 1,3-oxathiolanes.The cleavage of the 1,3-dithiolanes takes place by a more complicated mechanism with the formation of the disilyl ether of ethanediol, hexaethyldisilylthiane, and triethyl(alkylthio)silanes.The cyclic ortho thioester reacts with triethylsilane both at zinc iodide and at reduced nickel with the formation of the products from preferential cleavage of the exocyclic bond.
