76480-01-8Relevant academic research and scientific papers
Competing SNAr displacements of nitrite and SN2 displacements on the alkyl groups of alkyl p-nitrobenzoates and o-nitrobenzoates
Logue, Marshall W.,Han, Byung Hee
, p. 1638 - 1642 (2007/10/02)
Several p-nitrobenzoate and o-nitrobenzoate esters have been found to undergo competing SNAr and SN2 reactions with azide, alkoxide, and thiophenoxide ions. SNAr displacement of the nitro group even competes with SN2 displacement on the methyl group of methyl esters 1c and 11. Esters 1a and 1b undergo predominately SNAr displacements with azide, whereas 1c undergoes predominately an SN2 displacement with azide. Both 1b and 1c undergo predominately SNAr reactions with alkoxides and thiophenoxide. The SNAr products from the azide reactions consist of mixtures of p-azidobenzoates, p-aminobenzoates, and 4,4′-azodibenzoates whose compositions depend upon the reaction conditions.
