Tetrahedron p. 2293 - 2302 (1987)
Update date:2022-07-30
Topics:
Carboni, Bertrand
Toupet, Loic
Carrie, Robert
Depending on the nature of the substituent R2, diaziridines (I) react with dimethylacetylenedicarboxylate to give either iminoenamines or enamidines. When R1 = H and R2 = CH3 only one diastereoisomer is transformed, i.e. 1' and, then, 1' is isolated in a pure form. The knowledge of the stereochemistry of and of the structure of the obtained products allow a discussion of the mechanism of the reaction. The addition of picric acid to a mixture of diaziridines 1' and 1' leads to the picrate of 1' which, on treatment with sodium carbonate, gives this isomer pure.
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