Studies on the nitrosation ofN-silylated cyclopentenylamines

Abstract

The diazotization of N-silylated N-methyl-and N-phenylcyclopentenylamines affords products derived from intermediate methyl-and phenyldiazonium ions. However, when this method is applied to N,N-bissilylated cyclopentenylamines, the products obtained do not confirm the formation of a cyclopentenyl cation intermediate.

Facile Generation of a Strained Cyclic Vinyl Cation by Thermal Solvolysis of Cyclopent‐1‐enyl‐λ3‐bromanes

“…These results indicate that even these super‐ and hyperleaving groups will not be good enough leaving groups to produce strained cyclopent‐1‐enyl cation by thermal solvolysis. The attempt to generate the cyclopent‐1‐enyl cation by diazotization of N ‐silylated cyclopent‐1‐enylamines was also found to be fruitless 12. Herein, we report the first solvolytic generation of the five‐membered cyclic vinyl cation with a singlet ground state from cyclopent‐1‐enyl‐λ 3 ‐bromanes 6 , where the reaction proceeds at a reasonable rate even at room temperature.…”