Quinone Methide Generation Based on a cis-(N,N) Platinum Complex

Quinone methides (QMs) are highly reactive compounds that play important roles in various chemical and biological processes. In this work, a stable imino-pyridine platinum(IV) complex that bears a silyl-protected oxy-benzyl precursor of the quinone methide BHT−QM, derived from the food preservative 2,6-di-tert-butyl-4-methylphenol (BHT), was prepared and fully characterized, including by X-ray structural characterization. De-silylation results in a rarely observed, fully characterized, zwitterionic intermediate η1-methylene-p-phenoxy-Pt(IV), which undergoes de-aromatization to the unstable BHT−QM, which was trapped in solution.