102061-47-2Relevant academic research and scientific papers
Reduction of Vinylogous Thioesters with Lithium Aluminum Hydride. II. Reduction of 2-Methyl-3-phenylthio-5-substituted-2-cyclopentenones
Matoba, Katsuhide,Morita, Takashi,Yamazaki, Takao
, p. 3001 - 3005 (2007/10/02)
2,5-Dimethyl-3-phenylthio-2-cyclopentenone (IIb) and 5-tert-butyl-2-methyl-3-phenylthio-2-cyclopentenone (IIc) were reduced with an excess of lithium aluminum hydride (LAH) in ether to give quantitatively the corresponding 1,2-addition products, 2,5-dimethyl-3-phenylthio-2-cyclopentenol (IIIb) and 5-tert-butyl-2-methyl-3-phenylthio-2-cyclopentenol IIIc, respectively.Compound IIIb was transformed into the vinylsulfide (IVb) and the enone (Vb) on standing at room temperature, whereas (IIIc) was transformed into the diene (VII). 5-tert-Butyl-2-methyl-3-phenoxy-2-cyclopentenone (IX) gave 3-tert-butyl-1-methyl-5-phenoxycyclopentene (XI) in 63.1percent yield on reduction with LAH in ether.Keywords-vinylogous ester; vinylogous thioester; reduction; lithium aluminum hydride; 3-phenylthio-2-cyclopentenone
