4-T-Butylcyclohexenone

Interestingly, the hydrocyanation of 4-t-butylcyclohexenone gave, as the kinetic product, not the cis (124) but the trans cyanoketone 123. We have seen that there is good evidence that stereoelectronic effects play an important role in the hydrocyanation of conjugated ketones. Consequently, this result can be explained by the above steric argument on the basis of which the formation of the cis isomer 124 is disfavored. 

With knowledge that 7i-bond twisting is a factor in leading to the Type C rearrangement, we turned to study the 3-t-butylcyclohexenone 52 in Scheme 8.13. The introduction of... 

---