Generation of an N-isocyanatoimine and its cycloadditions leading to sterically stabilised zwitterions
Abstract
The reaction between 1,3-dimesitylbenzo[c]furan and 4-phenyltriazoline -3,5-dione affords a sterically stabilised zwitterion that 110 °C decomposes to the N-isocyanatoimine (13) which adds to olefinic and acetylenic traps to form stable zwitterions of the type (6) and (9), respectively; (9) isomerises to (10) at 110 °C.