A. Hudson et al., FREE-RADICALS FROM CYCLIC ENONES - AN ELECTRON-PARAMAGNETIC-RESONANCEINVESTIGATION - PART II - RADICAL ADDITIONS, Journal of the Chemical Society. Perkin transactions. II (Print), (10), 1998, pp. 2255-2260
The addition of silyl and germyl radicals to a series of substituted c
yclopentenones and cyclohexenones has been investigated using EPR spec
troscopy. At low temperatures the 3-position is the preferred site for
addition unless it is substituted or sterically hindered in which cas
e addition occurs at the carbonyl oxygen. The latter process is also f
avoured at higher temperatures but no evidence has been obtained for e
ither addition at the 2-position or for an intramolecular migration fo
llowing initial attack at the 3- or 2-position.