Competing Processes in Radiolytic Redistribution of Functional Groups in Alkyl Salicylates

Radiolysis of methyl salicylate (MS) and 2-ethylhexyl salicylate (ES) led to a wide variety of final products with overall yields of 105 and 236 nmol/J, respectively. Dealkylation and hydroxylation products predominated. The addition of methyl to the benzene ring was more probable in MS, while the formation of aliphatic hydrocarbons predominated in ES. The degradation of carboxyl groups in ES was an order of magnitude more effective than that in MS. It led to the predominant formation of salicylic acid and 2-ethylhexanol-1 in MS and ES, respectively. The yield of CO elimination in MS was almost an order of magnitude lower than that in ES. Dimers with C–C bridges between the benzene rings predominated among the heavy products in MS, whereas the amount of dimers with C–C and C–O–C bridges between side substituents was greater in ES.