129247-05-8Relevant articles and documents
1,3-DIPOLAR CYCLOADDITION REACTIONS OF YLIDES FORMED FROM PYRIDINES AND DICHLOROCARBENE
Khlebnikov, A. F.,Kostik, E. I.,Kostikov, R. R.,Bespalov, V. Ya.
, p. 304 - 311 (2007/10/02)
Pyridinium dichloromethylides, generated from substituted pyridines and dichlorocarbene, react endo-stereoselectively with dimethyl maleate to give substituted 3,3-dichloro-1,2,3,8a-tetrahydroindolizine-1,2-dicarboxylic acid dimethyl esters; the latter compounds are readily dehydrochlorinated and dehydrogenated to give the corresponding indolizine derivatives.Reaction of 3-substituted pyridines with dichlorocarbene and dimethyl maleate leads predominantly to the formation of 8-substituted indolizines.Cycloaddition of 4-picolinium dichloromethylide to unsymmetrical dipol arophiles occurs regioselectively.The observed selectivity in these reactions is consistent with predictions made on the basis of PMO theory.