15315-38-5Relevant academic research and scientific papers
Kinetics and Mechanism of the Nucleophilic Displacement Reactions of Chloroacetanilide Herbicides: Investigation of α-Substituent Effects
Lippa, Katrice A.,Demel, Sandra,Lau, Irvin H.,Roberts, A. Lynn
, p. 3010 - 3021 (2004)
The ease with which α-chloroacetanilide herbicides undergo displacement reactions with strong nucleophiles, and their recalcitrance toward weak ones, is intimately related to their herbicidal properties and environmental chemistry. In this study, we investigate the kinetics and mechanisms of nucleophilic substitution reactions of propachlor and alachlor in aqueous solution. The role played by the α-amide group was examined by including several structurally related analogs of propachlor possessing modified α substituents. The overall second-order nature of the reaction, the negative ΔS? values, the weak influence of ionic strength on reactivity, and structure-reactivity trends together support an intermolecular SN2 mechanism rather than an intramolecular reaction for α-chlomacetanilides as well as the a-chlorothioacetanilide analog of propachlor. In contrast, the α-methylene analog exhibits kinetics and a salt effect consistent with anchimeric assistance by the aniline nitrogen. Electronic interactions with the α-anilide substituent, rather than neighboring group participation, can be inferred to govern the reactivity of α-chloroacetanilides toward nucleophiles.
Cascade synthesis of spirooxindole δ-lactone derivatives through N-aryl hydroxymethylacrylamides with xanthates
Wang, Shucheng,Huang, Xuhu,Wen, Yanzhao,Ge, Zemei,Wang, Xin,Li, Runtao
supporting information, p. 8117 - 8122 (2015/12/30)
A novel and highly efficient cascade synthesis of spirooxindole δ-lactone derivatives from N-aryl hydroxymethylacrylamides and xanthates in good yields is described. The reaction proceeds through a radical addition/cyclization and ester exchange, in which two new C-C bonds and one C-O bond were formed.
