Thermal [2+2] Cycloaddition of Allenynes: Easy Construction of Bicyclo[6.2.0]deca-1,8-dienes, Bicyclo[5.2.0]nona-1,7-dienes, and Bicyclo[4.2.0]octa-1,6-dienes

详细信息    查看全文

• 作者：Chisato Mukai ; Yasuyuki Hara ; Yusuke Miyashita ; Fuyuhiko Inagaki
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：June 8, 2007
• 年：2007
• 卷：72
• 期：12
• 页码：4454 - 4461
• 全文大小：180K
• 年卷期：v.72,no.12(June 8, 2007)
• ISSN：1520-6904

文摘

The simple refluxing of allenynes, having a phenylsulfonyl functionality on the allenyl group, in xylene(or mesitylene) without microwave irradiation resulted in the efficient formation of bicyclo[5.2.0]nona-1,7-dienes and bicyclo[4.2.0]octa-1,6-dienes in high yields. This method was shown to be successfullyapplicable to the first construction of bicyclo[6.2.0]deca-1,8-dienes. Construction of the correspondingoxa- and azabicyclo[m.2.0] frameworks could also be attained. This thermal ring-closing reaction involvesthe formal [2+2] cycloaddition in which the distal double bond of an allenyl moiety exclusively servedas one of the -components regardless of the position of the phenysulfonyl functionality on the allenylmoiety.