Unexpected hydrogenation of C-C-double bonds with tert-butyl iodide
Unexpected hydrogenation of C-C-double bonds with tert-butyl iodide
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DOI：
10.1002/prac.19983400415
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发表时间：
1998-01-01
期刊：
影响因子：
--
通讯作者：
Liebscher, J
中科院分区：
文献类型：
--
作者：
Jin, SD;Liebscher, J
将3-异丁基亚基-2，5-二酮哌嗪1或4、马来酰亚胺或2，3-二氯-5，6-二氰基-对苯醌与叔丁基碘在甲苯中加热，引起共轭C-C-双键的氢化，分别得到3-异丁基二酮哌嗪2（外消旋）和3（外消旋）、琥珀酰亚胺或2，3-二氯-5，6-二氰基氢醌。此外，一个有趣的N-O-迁移的苯甲酰基以及还原芳构化为吡嗪5和6，分别观察到。
Heating of 3-isobutylidene-2,5-diketopiperazines 1 or 4, maleinimide or 2,3-dichloro-5,6-dicyano-p-benzoquinone with tert-butyl iodide in toluene gave rise to hydrogenation of the conjugated C-C-double bond affording 3-isobutyldiketopiperazines 2(rac) and 3(rac), succinimide, or 2,3-dichloro-5,6-dicyanohydroquinone, respectively. Furthermore, an interesting N-O-migration of a benzoyl group as well as reductive aromatization to pyrazines 5 and 6, respectively, were observed.