Abstract
Structures and Isomerisation of the 1,3‐Dipolar Cycloadducts of Dimethyl Maleate and Fumarate to 3‐Pyrazolidone‐azomethiniminesThe 1,3‐dipolar cycloaddition of dimethyl maleate 1b and fumarate 5b to the 3‐pyrazolidone‐azomethinimine 2 is a stereospecific cisoid reaction yielding the perhydropyrazolo[1,2‐a] pyrazoles 3b/4b in the molar ratio of 2:1, and 6b/7b in the molar ratio 1:1. Starting with each of the 4 stereoisomers, epimerization, catalysed by alcoholate, results in all 4 of them 3b, 4b, 6b and 7b with 7b as sterically favoured main product. During the addition reaction no epimerization is occurring. 1H‐ and 13C‐n.m.r. data are discussed.
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