American Chemical Society
jo990226o_si_001.pdf (734.29 kB)

Effect of β-Substituents on the Regioselectivity of the Diazomethane Ring Expansion of α-Methyl-α-methoxycyclobutanones to Cyclopentanones

Download (734.29 kB)
journal contribution
posted on 1999-04-07, 00:00 authored by Lisa M. Reeder, Louis S. Hegedus
The ring expansion of 22 differently β-substituted α-methyl-α-methoxycyclobutanones by diazomethane was studied. Migration of the less-substituted α-carbon was favored with the single exception of a very sterically hindered β-benzyloxy β-substituent.