Reaction of phenylcarbene formed from BENZALDEHYDE TOSYLHYDRAZONE (cas 1666-17-7) in certain solvents

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 CC bonds and insertion products of (IV) to aliphatic and to aromatic CH bonds. The reaction with aniline yields an insertion product of (IV) to the NH 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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