77695-74-0Relevant academic research and scientific papers
THROUGH-SPACE ELECTROSTATIC CONTROL IN A NOVEL REGIOSPECIFIC RING TRANSFORMATION OF 1,3,4-TRISUBSTITUTED MALEIMIDES
Seres, J.,Naray-Szabo, G.,Sinom, K.,Daroczi-Csuka, K.,Szilagyi, I.,Parkanyi, L.
, p. 1565 - 1570 (2007/10/02)
Ring transformation of 1-ethoxycarbonyl-3,4-disubstituted maleimide in alkaline solution yielded exclusively 1,5-disubstituted orotic acid.No hydantoin derivatives were detected.These findings can be best explained by assuming that the initial attack of the hydroxylate anion occurs at C2 and not at C5.X-ray diffraction and quantum chemical investigation indicate that stereospecificity is mainly due to through-space electrostatic effects.
