Journal of Organic Chemistry p. 2646 - 2651 (1992)
Update date:2022-08-04
Topics:
Hinton, Randall D.
Janzen, Edward, G.
Synthesis of C-phenyl-N-tert-butylnitrone (PBN) and several of its analogues with substituents in the 2-, 3-, or 4-position on the phenyl ring is described.While a one-pot reduction/condensation method proved suitable for the most compounds, it was necessary to prepare some examples by direct condensation or through oxidation of the appropriate imine.The 1H NMR data for the 3-X- and 4-X-PBN's can be correlated with the Hammett equation.For the 3-X series Δδ for the α-proton correlates best with ?+ and has a correlation coefficient of 0.90.For the 4-X series a dual substituent parameter equation using ?R0 gives the best correlation with r = 0.99.The hyperfine splitting constants (hfsc's) of HO<*> and HOO<*> adducts of serveral substituted PBN's are also included and their correlation with the Hammett equation is discussed.
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