Synthesis of naphthalenophane-type macrocyclic compounds using Mn(III)-based dihydrofuran-clipping reaction

摘要

The Mn(III)-based oxidation of 2,7-, 1,8-, and 1,5-disubstituted naphthalenes bearing both the 1,4-dioxa-7,7-diphenylhep-6-enyl and 1,4-dioxa-5,7-dioxooctyl groups gave new [12]naphthalenophanes along with the corresponding diploids via assembly of the dihydrofuran ring. A similar reaction of the 2,6-disubstituted naphthalene having the same substituents did not produce the naphthalenophane, but the diploid, [12,12](2,6)naphthalenophane, was obtained in a small amount. The 2,6-disubstituted naphthalene tethered to the 1,4,7-trioxa-10,10-diphenyldec-9-enyl and 1,4,7-trioxa-8,10-dioxoundecyl groups also underwent the dihydrofuran-clipping reaction to afford a trace amount of the desired [18](2,6)naphthalenophane. The reaction details and the structure determination of the products are described. (C) 2016 Elsevier Ltd. All rights reserved.