Oxidative Cyclopropanol Opening by Cob(III)alamin

Article abstract of DOI:10.1002/hlca.19840670606

Starting from the cyclopropanol 2, the isomeric cyclopropanol 4 and th β,γ-unsaturated aldehydes 7 and 8 have been produced by a cobalamin-dependant transformation.In traces, the two acetoxycyclopropanes 3 and 6, the saturated aldehydes 5 and 11 and the β,γ-unsaturated aldehyde 9 could be detected (cf.Structural Formulae and Table).Starting from 4 the same products in a rather similar distribution were obtained.The isomerization 2<*>4 as well as the transformations leading to 7, 8, and 9 are shown to be mediated by cob(III)alamin (1(III)).The results are explained on the basis of rearranging Co-complexes.The migrations might driven by the elctrophilic nature of the central Co(d6)-atom.