Tetrahedron p. 1565 - 1570 (1981)
Update date:2022-08-05
Topics:
Seres, J.
Naray-Szabo, G.
Sinom, K.
Daroczi-Csuka, K.
Szilagyi, I.
Parkanyi, L.
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.
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