380883-31-8Relevant articles and documents
Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated syntheses
Baguley, Paul A.,Jackson, Leon V.,Walton, John C.
, p. 304 - 309 (2002)
Synthetic routes to pure 1-phenylcyclohexa-2,5-diene-1-carboxylic acid and derived esters were developed. Esters containing appropriately unsaturated side chains generated the corresponding alkenyl radicals and hence gave good yields of 5-exo ring closure products in organotin-free reactions. Extrusion of phenyl radicals from the intermediate cyclohexadienyl type radicals was not observed, and this alternative β-scission did not compete under any conditions. Yields from alkylations of olefins in analogous intermolecular processes were, however, poor. As a spin-off from the research, it was found that 1-phenylcyclohexa-2,5-diene-1-carboxylic acid (6) was a useful source of hydroxyformyl (formate) radicals in organic solvents.
