Long-Lived Carbocations: Generation from 5,5,10,10-Tetramethyl-5,10-dihydroindeno[2,1-a]indene, Structure, and Rearrangements

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• 作者：Genaev ; A. M. ; Sal'nikov ; G. E. ; Shubin ; V. G.
• 刊名：Russian Journal of Organic Chemistry
• 出版时间：2001
• 出版年：2001
• 期刊代码：33_10704280
• 类别：ph
• 卷：37
• 期：9
• 页码：1255-1258
• 数据来源：sp

摘要

According to the NMR data, protonation of 5,5,10,10-tetramethyl-5,10-dihydroindeno[2,1-a]indene in the system HSO$\_3$F-SO$\_2$ClF-CD$\_2$Cl$\_2$ at -80°C gives rise to long-lived 5,5,10,10-tetramethyl-2H-5,10-di- hydroindeno[2,1-a]indenium ion which undergoes isomerization into 4b,5,10,10-tetramethyl-4b,5,9b,10-tetra- hydroindeno[2,1-a]inden-5-yl cation on raising the temperature. On the basis of the data obtained for rear- rangements of such carbocations an alternative mechanism has been proposed for the rearrangements of struc- turally related carbocations having a bicyclo[3.3.0]octane skeleton.