Reaction of bis(bis(trimethylsilyl)amido)mercury(II) with 3,3 '-disubstituted binaplithols: Cyclization via an intramolecular electrophilic aromatic substitution reaction

摘要

Reaction of the mercury(II) amide Hg[N(SiMe3)(3)](2) with 3,3'-disubstituted binaphthols (HO)(2)C20H10(R)(2)-3,3' (R = SiMe3, SiMe2Ph, SiMePh2, SiPh3) in a 2:1 stoichiometric ratio furnishes four hexacyclic 1,7-disitylsubstituted derivatives of peri-xanthenoxanthene (PXX). Reaction of these two reagents in a 1: 1 ratio results in a mixture of the hexacyclic products as well as the related pentacyclic species which contain one hydroxyl group and only one C-O-C ring fusion. The structures of three of the hexacyclic products (R = SiMe3, SiMe2Ph, SiMePh2) and one of the pentacyclic products (R = SiMe3) have been obtained. The reaction of Hg[N(SiMe3)(3)](2) with the 3,3'-disubstituted binaphthols proceeds via an intramolecular electrophilic aromatic substitution reaction and several intermediates in this process have been detected using NMR (H-1 and Hg-199) spectroscopy. (c) 2006 Elsevier B.V. All rights reserved.