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Reactions of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo-[3.3.1]non-7-en-6-one at the carbonyl group
Authors:L A Baeva  A D Ulendeeva  A A Fatykhov  N K Lyapina
Institution:1.Institute of Organic Chemistry, Ufa Research Center,Russian Academy of Sciences,Ufa,Bashkortostan, Russia
Abstract:The reduction of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo3.3.1]non-7-en-6-one with aluminum hydride, lithium tetrahydridoaluminate, or lithium tris(tert-butoxy)hydridoaluminate in tetrahydrofuran gave 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo3.3.1]non-7-en-6-ol. 8-Methyl-5-methylsulfanylmethyl-3-thiabicyclo3.3.1]nonan-6-ol was obtained by reduction of the title compound with sodium tetrahydridoborate in pyridine or dimethylformamide. The reaction of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo3.3.1]non-7-en-6-one with hydroxylamine hydrochloride afforded the corresponding oxime.
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