Study and comparison of the pH-independent hydrolysis of eight alkyl nitrites shows 3-nitroso-1,2-glyceryl dinitrate, a putative intermediate in the biotransformation of glyceryl trinitrate, to be unexpectedly reactive and too labile to be detected as a biotransformation intermediate in aqueous solution, suggesting a role for neighbouring group participation by the β-nitrate group.
F. Buckell, J. D. Hartry, U. Rajalingam, B. M. Bennett, R. A. Whitney and G. R. J. Thatcher, J. Chem. Soc., Perkin Trans. 2, 1994, 401 DOI: 10.1039/P29940000401
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