3463-90-9Relevant academic research and scientific papers
Regioselectivity in the 1,3-Dipolar Cycloaddition Reaction of Unsymmetric Pyridinium Dicyanomethylides with Dimethyl Acetylenedicarboxylate and Methyl Propiolate: An Example of Dipole-Dipole Control of Regioselectivity?
Matsumoto, Kiyoshi,Ikemi, Yukio,Konishi, Hideyuki,Shi, Xiao-lan,Uchida, Takane,Aoyama, Kinuyo
, p. 689 - 692 (2007/10/02)
A study of the cycloaddition behavior of a series of unsymmetric pyridinium dicyanomethylides with dimethyl acetylenedicarboxylate and methyl propiolate has been carried out.The 1,3-dipolar cycloaddition proceeds in good yield with high regioselectivity to produce the corresponding indolizines and 1:1 adducts.The reactions of isoquinolinium dicyanomethylide follow frontier orbital predictions.In contrast, polar 3-substituted pyridinium dicyanomethylides gave predominantly the corresponding 8-isomers regardless of the substituents.The results can be explained by dipole-dipole interactions.
