Abstract
A series of novel heteropentalene mesomeric betaines, pyrrolo[1,2-c]imidazole mesomeric betaines (I) were prepared by condensation of 2-formylpyrroles with aromatic imines. The mesomeric structures I are proposed on the basis of spectral and microanalytical data and the results of their participation in 1,3-dipolar cycloaddition reactions. Peri-, regio-, and stereoselectivity of cycloadditions of mesomeric betaines I with acetylenic (DMAD, ethyl propiolate, ethyl phenylpropiolate, benzyl phenylpropiolate, and phenylacetylene) and olefinic (dimethyl fumarate and dimethyl maleate) dipolarophiles have been studied. The respective formation of 2,2'-bipyrroles and 2,3'-dihydro-2,2'-bipyrroles in the cycloaddition of acetylenic and olefinic dipolarophiles could be rationalized by considering rearrangements of the expected bicyclic cycloadducts
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