HOMOALLYLIC SUBSTITUTION REACTIONS OF LITHIUM DIALKYL CUPRATES WITH CYCLOPROPYLCARBINYL HALIDES: MECHANISTIC CONSIDERATIONS

Article abstract of DOI:10.1016/S0040-4020(01)91792-2

Highly reactive lithium dialkyl cuprates and 1-bromo-1-cyclopropylalkanes, 4, react to give good yields of the homoallylic substitution product, 6.Less reactive organocuprates react with 4 to give mixtures of 6 and the direct substitution product 7.These results are consistent with a copper(I) radical intermediate which undergoes facile rearrangement prior to reductive coupling.