Azulene-Naphthalene-Type Rearrangements in Benz[a]azulene and Cyclohepta[b]indole

详细信息    查看全文

• 作者：Prof. Dr. Curt Wentrup and Dr. Jü ; rgen Becker
• 刊名：Chemistry - A European Journal
• 出版年：2016
• 出版时间：September 19, 2016
• 年：2016
• 卷：22
• 期：39
• 页码：13835-13839
• 全文大小：432K
• ISSN：1521-3765

文摘

Flash vacuum pyrolysis (FVP) of benz[a]azulene yields phenanthrene and 2-ethynylbiphenyl. FVP of cyclohepta[b]indole similarly yields phenanthridine and 2-cyanobiphenyl. The reversibility of the reactions is demonstrated by FVP of 2-ethynylbiphenyl and 2-isocyanobiphenyl. All the observed reactions are in accord with the norcaradiene–vinylidene mechanism of the azulene–naphthalene rearrangement, whereas other proposed mechanisms are ruled out.