A SHORT NEW AZULENE SYNTHESIS

A SHORT NEW AZULENE SYNTHESIS
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DOI:
10.1021/ja00540a023
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发表时间:
1980-01-01
影响因子:
15
通讯作者:
KIRMS, MA
KIRMS, MA
中科院分区:
化学1区
文献类型:
--
作者:
SCOTT, LT;MINTON, MA;KIRMS, MA

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A short new azulene synthesis, requiring no dehydrogenation step, has been developed (Scheme I). Intramolecular carbene addition creates the bicyclic ring system of azulene with a high degree of unsaturation and versatile functionality in a single step from a simple benzene derivative. The synthesis is particularly amenable to preparation of specific 13C-and 2H-labeled azulenes.Azulene, the first and best known of all nonbenzenoid aromatic hydrocarbons, has played a major role in the advancement of our understanding of cyclicconjugation. 1 Since Planner’s original synthesis of this unusual, blue hydrocarbon in 1937, 2 a variety of new pathways to azuleneshas been reported. 3 Prominent