Synthesis of functionalized phenolic derivatives via the Benzannulation of dienylketenes formed by a thermal Wolff rearrangement of alpha-diazo-beta-keto compounds
Synthesis of functionalized phenolic derivatives via the Benzannulation of dienylketenes formed by a thermal Wolff rearrangement of alpha-diazo-beta-keto compounds
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DOI：
10.1016/0040-4020(96)00318-3
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发表时间：
1996-05-06
期刊：
影响因子：
2.1
通讯作者：
Doutheau, A
中科院分区：
文献类型：
--
作者：
Collomb, D;Deshayes, C;Doutheau, A
以α，β-不饱和羰基化合物为原料，合成了11个共轭二烯基α-重氮-β-酮衍生物。它们的热处理引起Wolff重排，产生中间体二烯基烯酮，其具有所需内部双键构型的异构体经历苯并环化，从而形成相应的酚衍生物。当被甲氧基γ-取代时，重氮化合物的两种立体异构体由于中间体环丁烯酮的可逆形成而产生酚衍生物，所述中间体环丁烯酮允许非生产性瞬时二烯基烯酮异构化为生产性二烯基烯酮。版权所有（C）1996 Elsevier Science Ltd
Eleven conjugated dienyl alpha-diazo-beta-keto derivatives were prepared from alpha,beta-unsaturated carbonyl compounds. Their thermolysis induced a Wolff rearrangement generating an intermediate dienyl ketene whose isomer which has the required configuration of the internal double bond underwent a benzannulation thus forming the corresponding phenolic derivatives. When gamma-substituted by a methoxy group both stereoisomers of the diazo compounds gave rise to the phenolic derivatives due to the reversible formation of an intermediate cyclobutenone which permitted the isomerization of the nonproductive transient dienylketene into the productive one. Copyright (C) 1996 Elsevier Science Ltd