119018-56-3Relevant academic research and scientific papers
Tributylstannane-Mediated Cyclization of Thionocarboxylic Acid Derivatives
Bacchi, Mario D.,Bosch, Eric,Denenmark, Daniella,Girsh, Diana
, p. 6803 - 6810 (2007/10/02)
Cyclization reactions of various thionoesters and thioamides involving the addition of tri-n-butylstannyl radical to a thiocarbonyl group and intramolecular addition of the resulting radical to a carbon-carbon multiple bond was studied.Dithiocarbonate and (imidazolyl)thiocarbonyl derivatives of homoallylic alcohols gave α-substituted γ-thionobutyrolactones.The reaction is highly dependent on the substitution pattern on the double bond, a high yield of products being obtained only when the double bond is activated and unhindered. (Z)-4-Phenylbut-3-enyl thionobenzoate afforded 4,5-dihydro-2-phenyl-3-benzylfuran in low yield.In reactions involving a thioamide group, good yields of cyclic products were obtained only from compounds in which the electron density on the nitrogen atom is decreased by an electron attracting group.Cyclization of 1-((E)-4-phenylbut-3-en-1-yl)-5-thioxopyrrolidin-2-one (23) afforded 1-aza-4-benzylbicyclooct-4-en-8-one (33).
Free Radical Cyclization of Thionocarbonic Acid Derivatives of 4-Phenyl-3-butenol. A New Route to Thionolactones
Bachi, Mario D.,Bosch, Eric
, p. 1234 - 1236 (2007/10/02)
Treatment of various thionocarbonic acid derivatives of 4-phenyl-3-butenol with tri-n-butyltin hydride and AIBN in boiling benzene provides thionolactones and lactones in good yields via a free radical chain reaction.
On the Mechanism of Reductive Degradation of Dithiocarbonates by Tributylstannane
Bachi, Mario D.,Bosch, Eric
, p. 1517 - 1520 (2007/10/02)
Product analysis of the reaction between O-isopropyl S-4-phenylbut-3-enyl dithiocarbonate and tributylstannane, initiated by azoisobutyronitrile in boiling benzene or toluene, indicates that the first step in the reductive of dithiocarbonates by trialkyls
