Abstract
Aniline adducts of α-nitrostilbenes, PhCH(HNC 6 H 4 Z)CH(C 6 H 4 Y)NO 2 ha- ve been synthesized for a variety of Z/Y combinations. In several cases a mixture of two diastereomers was obtained. Structural assignment of the diastereomers was based both on 1 H NMR and reactivity data. The kinetics of the breakdown of the adducts into the respective benzalani- lines and arylnitromethane anions was studied in acidic 50% Me 2 SO-50% water solutions at 5 o C. The rate constants, k exp , were found to be independent of buffer concentration and pH, indicating a unimolecular mechanism. There is a strong dependence on the aniline substituent (ρ = -2.2) and the pK a of the arylnitromethanes (β 1g =-1.28).
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