Syntheses of Calixnaphthalenes Derived from 1-Naphthol

Article abstract of DOI:10.1021/jo00127a038

Using a convergent synthetic strategy, the synthesis of the previously elusive C_4ν-symmetrical calix<4>naphthalene from 1-naphthol is described.Using other independent convergent routes, syntheses of the other three isomeric calix<4>naphthalenes originally formed from the direct base-catalyzed condensation of formaldehyde with 1-naphthol are also described.All of these methods involved either a TiCl4- or TFA-assisted coupling reaction to achieve the cyclization steps.A mechanism is proposed to account for the formation of the original three isomeric calix<4>naphthalenes from the base-catalyzed condensation of formaldehyde with 1-naphthol.