N-Octyl lithium

The effect of penultimate units on the rate constants of anionic propagation is observed also in other systems. For example, the addition of styrene to the lithium salt of 1-phenyl-n-hexyl anion is 4 times faster than to polystyryl lithium 51). Similarly, the addition of monomer to the lithium salt of 1,1-diphenyl-n-hexyl lithium is faster than the addition to 1,1,3-triphenyl-n-octyl lithium or 2-poly-sty ry 1-1,1-diphenyl ethyl lithium, the latter two salts having comparable reactivities52 . See also Ref.53)... 

Reconnection to the lactone 46 then provides a means of controlling the stereochemistry using the Baeyer-Villiger rearrangement of the cyclohexanone 47. Acylation of the lactone 46 with n-octyl-lithium at low temperatures gives a 70% yield of the hydroxyketone 48, which in turn gives the pheromone 43. 

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