Abstract
Anti-8-methoxy[2.2]metacyclophanes (MCPs) 5 a–b were obtained via pyrolysis of the corresponding syn-thiatetraoxide cyclophanes 4 a–b. Coupling reactions of 4-tert-butyl-1-methoxy-2,6-bis(mercaptomethyl)benzenes 1 a–b and 1,5-bis(chloro-methyl)-2,4-dimethylbenzene 2 under high dilution conditions afforded only the syn-conformers of 9-methoxy-2,11-dithia[3.3]metacyclophanes 3 a–b, which with m-CPBA formed the corresponding syn-tetraoxides 4 a–b. Lewis acid (TICl4/AlCl3-MeNO2) or iodine-catalyzed reactions of 5 b under various conditions led to transannular cyclization to afford tetrahydropyrene 6 b and pyrene derivative 7 b and/or de-tert-butylated 6 a. Iodine-catalyzed reaction of 5 a afforded tetrahydropyrene 6 a. These findings suggest the potential for a new route to alkylated pyrenes via strained and alkylated metacyclophanes. Density functional theory (DFT) studies were carried out to investigate the conformational characteristics of 3–5.
Original language | English |
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Pages (from-to) | 1269-1274 |
Number of pages | 6 |
Journal | ChemistrySelect |
Volume | 5 |
Issue number | 4 |
DOIs | |
Publication status | Published - Jan 31 2020 |
All Science Journal Classification (ASJC) codes
- Chemistry(all)