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25.6.6.10.2 Variation 2: In Situ Generation of Hydrogen Cyanide from 1,3,5-Triazine (Kreutzberger Modification)

DOI: 10.1055/sos-SD-025-00443

Schall, A.; Reiser, O.Science of Synthesis, (200725640.

1,3,5-Triazine (39) can be used as a source of hydrogen cyanide; however, yields are generally lower compared to the direct employment of cyanide (Table 18).[‌130‌,‌131‌] In the presence of hydrogen chloride, electron-rich arenes react with 1,3,5-triazine (39) to give the aldimine hydrochlorides 40, which are hydrolyzed to the corresponding aromatic aldehydes (Scheme 22). Less-activated arenes require stoichiometric amounts of a Lewis acid such as zinc(II) chloride or aluminum trichloride; nevertheless, even toluene can be formylated in good yields under these conditions.

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