Add time:09/24/2019 Source:sciencedirect.com
Treatment of BENZALDEHYDE TOSYLHYDRAZONE (cas 1666-17-7) (I) with sodium methoxide in various solvents under irradiation and/or heating yields products arising from phenylcarbene (IV) which is produced by photolytic or pyrolytic decomposition of initially formed phenyldiazomethane (III). Reaction products originating solely from the tosylhydrazone (I) are (VI ∼ XI) while those produced by the interaction with solvents are formulated as addition products of (VI) to olefinic and aromatic CC bonds and insertion products of (IV) to aliphatic and to aromatic CH bonds. The reaction with aniline yields an insertion product of (IV) to the NH bond, or N-benzylaniline, in 26% yield, besides ring-benzylated compounds. o-Toluadehyde and 2,4,6-trimethylbenzaldehyde tosylhydrazones react similarly.
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