Science of Synthesis

Cordero, F. M.; Cicchi, S., Science of Synthesis, (2005) 22, 312.

The reactions between nitrosoarenes ‌191‌ and N-methyleneamines ‌192‌, which are in equilibrium with the corresponding trimeric 1,3,5-arylhexahydro-1,3,5-triazine form, afford the 1:1 addition compounds in moderate yields (‌Scheme 59‌). The products appear to be the C-amino-N-arylnitrones ‌194‌ rather than the tautomeric N1-aryl-N1-hydroxyformimid­amides ‌193‌.[‌93‌,‌102‌] The structure in the solid state of ‌194‌ (Ar1 = Ph; R1 = 4-MeOC6H4) has been unambiguously confirmed by X-ray diffraction structure analysis, whereas spectroscopic data in dichloromethane-d2 suggest a rapid interconversion between the tauto­meric forms ‌193‌ and ‌194‌.[‌103‌]

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References