Intramolecular nucleophilic capture of radical cations by tethered hydroxy functions

Electron donor systems bearing tethered hydroxy functions are converted upon photo-induced electron transfer to mono-, bi-, or tricyclic ethers by intramolecular nucleophilic substitution or capture via four- to seven-membered transition states. Geraniol and nerol undergo tandem-cyclizations as 1,5- and/or 1,6-C-C cyclizations precede nucleophilic capture.