The reaction of diphenylnitrilimine with some arylidenebenzothiazinone dioxides leads to a mixture of two products that were isolated by chromatography. Spectroscopic data (infrared, nuclear magnetic resonance) and a radiocrystallographic study illustrate a competition between the two dipolarophilic sites in dipolar cycloaddition.

R e p le 27 juillet 1993 TAHAR LAKHLIFI, AHMED SEDQUI, TOUFIK FATHI, BERNARD LAUDE et JEAN-FRAN~OIS ROBERT. Can. J. Chem. 72,1417 (1994. La synthkse de sept 5-ph~nyl-3,4-dihydro-2H-pyrrole-2-carboxylates de mCthyle precurseurs d'ylures d'azomCthine cycliques pentagonaux 1 est dkcrite. Ces produits i caractere dipolaire rkagissent avec les N-methyl et N-phCnylmal6imides de fa~on diastCrCospCcifique. L'approche des reactants se fait sur la face la moins encombrke du dip81e-1,3 et en endo pour donner le cycloadduit thermodynamiquement le plus stable de structure exo. De plus, l'oxydation de ces composes 1 permet d'acceder aux pyrroles substituCs correspondants.TAHAR LAKHI~FI, AHMED SEDQUI, T o m FATHI, BERNARD LAUDE, and JEAN-FRAN~OIS ROBERT. Can. J. Chem. 72, 1417Chem. 72, (1994. Seven derivatives of methyl 5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylates 1 were synthetized. These compounds are precursors of pentagonal cyclic azomethine ylids, the two sides of which are diastereotopic. The 1,3-dipolar species react with N-methyl and N-phenylmaleimides diastereospecifically. The approach of the reactant species occurs from the less hindered side of the 1,3-dipole and in endo to lead the thermodynamically stable exo cycloadduct. Moreover, oxidation of the compounds 1 gives the corresponding substituted pyrroles.

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