Captodative substituent effects—XV : Generalisation of bridged dehydrodimerisation by varying radicophiles and polarity of attacking radicals

Abstract

Captodative olefins efficiently trap both electrophilic or nucleophilic radicals, i.e. various thiyl, acetyl, acetamidomethyl and N-methylanilinomethyl radicals. In the first three cases, good yields of adduct-dimers 4 are formed and these reactions are preparatively useful. In the last case when anilinomethyl radicals are formed at 140°, also dismutation or double adduct 5 formation may occur depending on the choice of c and d groups in 2.