The Fe⁰ Promoted Addition of CCI₄, and CCI₃Br to Olefins

Abstract

The radical addition of CCI₄ or CCI₃Br to olefins is efficiently promoted by iron filings in N,N-dimethylformamide under mild conditions.

Notes

The use of Mg(0),^4b,30 Mn(0),³¹ Cu(0)³² and Ni(0)^4b as initiators in radical halo-alkyl-additions with polyhalomethanes has been reported.

4-Octyne, an internal alkyne, gives some higher conversion than 1-octyne, but the main product derives from an unexpected HCl addition to the triple bond.

High headspaces negatively affect the reaction, owing to the partition of olefin and polyhalomethane between liquid and vapour phases. The best yields are obtained on working with Schlenk capacity little higher than the reaction volume.