No abstract

Diethylzinc can be used, in the presence of oxygen, as an efficient chain transfer reagent in radical additions to glyoxylate imines. Experimental evidence for the competition between radical and nucleophilic additions is given.

In the presence of oxygen, diethylzinc can be used to promote radical additions to CN bond containing radical acceptors and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reactions is established. The methodology is restricted to secondary and tertiaryalkyl radicals generated from the corresponding alkyl iodides. It could not be extended either to CC bond containing radical acceptors such as methyl methacrylate and nitrocyclohexene or to diethylazodicarboxylate.