Rate constants for the reactions of primary alkyl radicals with SmI2 in THF/HMPA
E Hasegawa, DP Curran - Tetrahedron letters, 1993 - Elsevier
… We chose 6-iodo-1-hexene (1) as the radical clock,5 and we propose the mechanistic
scheme outlined in eq 2 based on our studies on the mechanism of the samarium Barbier
and samarium Grignard reactions.sb Reduction of 1 by SmI2 produces the Z-hexenyl radical,6
which in turn partitions between further reduction to generate 2 and 5-exe-hexenyl … When
possible, we recommend that 5 equiv of HMPA per SmI2 be used to conduct radical
reactions. Under these conditions, reactions are rapid, reproducible and high-yielding, and …
scheme outlined in eq 2 based on our studies on the mechanism of the samarium Barbier
and samarium Grignard reactions.sb Reduction of 1 by SmI2 produces the Z-hexenyl radical,6
which in turn partitions between further reduction to generate 2 and 5-exe-hexenyl … When
possible, we recommend that 5 equiv of HMPA per SmI2 be used to conduct radical
reactions. Under these conditions, reactions are rapid, reproducible and high-yielding, and …