[4.2](2,2鈥?(2,2鈥?Biphenylophanetriyne: A Twisted Biphenylophane with a Highly Distorted Diacetylene Bridge

详细信息    查看全文

• 作者：Shunpei Nobusue ; Hiroshi Yamane ; Hirokazu Miyoshi ; Yoshito Tobe
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：April 4, 2014
• 年：2014
• 卷：16
• 期：7
• 页码：1940-1943
• 全文大小：249K
• 年卷期：v.16,no.7(April 4, 2014)
• ISSN：1523-7052

文摘

Biphenylophane 1 bridged by acetylene and diacetylene linkages was synthesized. X-ray analysis revealed its highly deformed diacetylene unit with a bond angle of 160掳. Enantiomers of 1 resolved by chiral HPLC underwent facile racemization with an activation energy of 90.6 kJ mol^鈥?. Transannular cyclization of 1 was induced by heating to generate benzyne intermediate 8, which was intercepted by furan to give 9, and by treatment with bromine to give dibromodibenzopicene (10).