QUINONES AND QUINONE-METHIDES .1. CYCLIZATION AND DIMERIZATION OF CRYSTALLINE ORTHO-QUINONE METHIDES FROM PHENOL OXIDATION REACTIONS
QUINONES AND QUINONE-METHIDES .1. CYCLIZATION AND DIMERIZATION OF CRYSTALLINE ORTHO-QUINONE METHIDES FROM PHENOL OXIDATION REACTIONS
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DOI：
10.1016/0040-4020(77)80122-1
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发表时间：
1977-01-01
期刊：
影响因子：
2.1
通讯作者：
JURD, L
中科院分区：
文献类型：
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作者：
JURD, L
2-肉桂基-4,5-亚甲二氧基苯酚的氧化银或2,3-二氯-5,6-二氰基苯醌氧化产生结晶邻醌甲基化物，其经历热或酸催化环化成6,7-亚甲基-二氧黄-3-烯。 2-(4-甲氧基苄基)-4,5-亚甲二氧基苯酚的氧化产生结晶邻醌甲基化物，其在极性溶剂中快速二聚。无色二聚体的结构是以前未报道的类型，表明其形成涉及离子反应。
Silver oxide or 2,3-dichloro-5,6-dicyanobenzoquinone oxidation of 2-cinnamyl-4,5-methylenedioxyphenol yields a crystalline o-quinone methide, which undergoes thermal or acid-catalyzed cyclization to 6,7-methylene-dioxyflav-3-ene. Oxidation of 2-(4-methoxybenzyl)-4,5-methylenedioxyphenol yields a crystalline o-quinone methide which rapidly dimerizes in polar solvents. The structure of the colorless dimer, which is of a type not previously reported, suggests that an ionic reaction is involved in its formation.