Diels-Alder reactions of vinyl derivatives of five-membered monoheterocyclic compounds

WE Noland, CK Lee, SK Bae, BY Chung…

Index: Noland, Wayland E.; Lee, Chang Kiu; Bae, Sun Kun; Chung, Bong Yul; Hahn, Chi Sun; Kim, Keun Jae Journal of Organic Chemistry, 1983 , vol. 48, # 15 p. 2488 - 2491

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Citation Number: 22

Abstract

Vinylpyrroles having electron-withdrawing substituents react with dienophiles to give [4+ 21 r adducts while the furan and thiophene analogues do not." he difference in reactivity among the monoheterocycles can be explained in terms of the greater electron-releasing ability of the nitrogen atom in the pyrrole. The s-cis conformation of the (1H-pyrrol-2-y1) maleate derivatives appears to be an important factor in their undergoing the cycloaddition ...