Cyanobenziodoxols 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystalline compounds. Cyanobenziodoxol 2 reacts with N,N-dimethylary lamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.
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Acknowledgement. This work was supported by a Cottrell College Science Award of Research Corporation; a research grant from the National Science Foundation (NSFXHE-9505868); a grant from the Donors of The Petroleum Research Fund, administered by the ACS; the University of Minnesota Graduate School Grant-in-Aid; the UMD Department of Chemistry Summer 1995 Undergraduate Research Program, and a Fellowship Award for A.J.S. from the CURSOR program.