期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 68, 期 12, 页码 4955-4958出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0340410
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The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN(3)) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl(2) as catalyst the reaction proceeds at 0 degreesC with a number of different propargyl sulfides in 31-73% isolated yield. The reaction is limited by product instability toward catalyst and termination of the catalytic cycle by excess BocN3. N-Allenylsulfenimide 2b smoothly undergoes catalytic hydrogenation and a Diels-Alder reaction with cyclopentadiene.
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