NOVEL METALATION OF BENZOTRIAZOLES AND ITS UTILITY IN THE SYNTHESIS OF 4-SUBSTITUTED OXINDOLES

Repeated metallation/silylation of 1-methoxymethylbenzotriazole 1 give s a high yield of the 4-tristrimethylsilyl benzotriazole derivative 5 which undergoes a high yielding fluoride-catalysed Peterson olefinatio n reaction to give -(4-trimethylsilylbenzotriazolyl)-methoxymethylene adamantane 6b. Photolysis of 6b affords a remarkably strained iminoeth er 7b which can easily be converted to the corresponding oxindole 9.