70769-74-3Relevant articles and documents
Attempted Simmon-Smith reaction on β-alkylthio-α,β- unsaturated ketones: A regiospecific synthesis of 2,4-disubstituted thiophenes
Swaroop, Toreshettahally R.,Roopashree, Rangaswamy,Ila, Hiriyakkanavar,Rangappa, Kanchugarakoppal S.
, p. 147 - 150 (2013/02/21)
A new regiospecific route to 2,4-disubstituted thiophenes has been developed through Simmon-Smith reaction on β-methylthio-α,β- unsaturated ketones. Extension of the reaction to β-ethyl/benzylthio- α,β-unsaturated ketones also gave the corresponding 2,4-disubstituted thiophenes in a regiospecific manner. A probable mechanism involving a carbenoid methylene insertion to divalent sulfur followed by intramolecular aldol condensation has been suggested.
Reduction of β-Arylthio- or β-Alkylthio-αβ-Unsaturated Ketones
Nishio, Takehiko,Omote, Yoshimori
, p. 934 - 938 (2007/10/02)
The preparation and reduction of β-arylthio or β-alkylthio-αβ-unsaturated ketones (1) with lithium aluminium hydride or sodium borohydride have been examined.Reduction of the ketones (1) with lithium aluminium hydride gave αβ-unsaturated ketones (2), in which the olefinic (R1) and carbonyl (R2) substituents are reversed compared with the starting αβ-unsaturated ketone (1), or the saturated γ-hydroxy-sulphides (3).Reduction of the ketones (1) with sodium borohydride afforded only the αβ-unsaturated ketones (2).Reduction of (1) with sodium borohydride in the presence of metal halides gave the saturated ketones (5).
