Page 725 - Advanced Organic Chemistry Part B - Reactions & Synthesis

701
TS-Va TS-XXe
SECTION 8.1
Li 1
Br O Organocopper
Li 1
Intermediates
CI
C 2
C
CI C 1
Li 2
Li 2
Cu
Cu
a
a
C H 3 C H 3
Fig. 8.4. Representation of the orbital involved in C–Cu bond
formation in the reaction of CH 3 2 CuLi-LiCl with methyl bromide
(left) and ethylene oxide (right). Reproduced from J. Am. Chem. Soc.,
122, 7294 (2000), by permission of the American Chemical Society.

Fig. 8.5. Computational reaction profile (B3LYP/631A) for reaction of CH 3 2 CuLi
2 with acrolein.
Adapted from J. Am. Chem. Soc., 119, 4900 (1997), by permission of the American Chemical Society.