Adamantylsulfanyl- and N-adamantylcarboxamido-derivatives of heterocycles and phenols: synthesis, crystal structure, tumor necrosis factor-alpha production-enhancing properties, and theoretical considerations.

The synthesis of several adamantylthio heterocycles and S-adamantylated thiocresols is reported. The attack of the adamantyl cation formed from 1-adamantan-1-ol in refluxing trifluoroacetic acid provides the corresponding adamantylsulfanyl compounds. The use of the adamantyl cation in the Ritter reaction gave the number of N-adamantylcarboxamide derivatives of heterocyclic and phenolic compounds.