Synthesis of Acyclic Polycarbonyl Compounds via Ozonolysis of Cyclohexa-1,4-dienes

Synthesis of Acyclic Polycarbonyl Compounds via Ozonolysis of Cyclohexa-1,4-dienes
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1,4-环己二烯臭氧分解合成无环多羰基化合物

DOI:
10.1055/s-0034-1380148
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发表时间:
2015
期刊:
Synthesis
影响因子:
--
通讯作者:
G. Hilt
G. Hilt
中科院分区:
--
文献类型:
--
作者:
J. Kuttner;G. Hilt

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钴催化的2-(三甲基硅氧基)丁酸-1,3-二烯与炔的Diels-Alder反应生成取代的环己烯-3-烯-1-酮,经臭氧氧化后可转化为多羰基衍生物。酮醛的Wittig烯化反应生成不饱和的多酮基衍生物,或者酮醛与伯胺和仲胺反应生成乙烯基酰胺。2,7-重氮-1-苯基-1,3,6,8-四酮在1,3-二羰基亚基上经2次重氮转移反应,得到环己烯-1,4-二酮主链。
Cobalt-catalyzed Diels–Alder reaction of 2-(trimethylsiloxy)buta-1,3-dienes with alkynes gives substituted cyclohex-3-en-1-ones that were converted into polycarbonyl derivatives upon ozonolysis. Wittig olefination of ketoaldehydes gave unsaturated polycarbonyl derivatives or alternatively the ketoaldehydes were reacted with primary and secondary amines to give vinylogous amides. 2,7-Didiazo-1-phenylnonane-1,3,6,8-tetraone underwent double diazo-transfer reaction at the 1,3-dicarbonyl subunits by rhodium-catalyzed cyclization to give the cyclohex-2-ene-1,4-dione backbone.