Tetrahedron p. 2683 - 2694 (1981)
Update date:2022-07-29
Topics:
Vincens, M.
Dumont, C.
Vidal, M.
The identification of E- and Z-2-alkyl-3-ethylidenecyclopropane having a functional group (ketone, ester, alcohol) at C-1 of the ring, is realized by chemical means and by NMR induced shift using Eu(dpm)3.These structure assignments show that the cyclopropene ester, ketone, alcohol double bond migration in basic media leads preferentially to the E-configuration; the stereoselectivity may reach 90percent.Moreover, the prototropy is regiospecific and stereospecific compared to the ring.
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