Synthesis and conformational studies of 9-benzyloxy-18-substituted [3.3]metacyclophanes

M. Monarul Islam, Tomiyasu Hirotsugu, Taisuke Matsumoto, Junji Tanaka, Takehiko Yamato

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8 Citations (Scopus)

Abstract

A series of syn-[3.3]metacyclophanes (MCPs) containing internal substituted benzyloxy group have been synthesized by the modified TosMIC coupling reaction followed by acid treatment and Wolff-Kishner reduction. anti-Mono-and di-benzyloxy[3.3]MCPs are synthesized by O-benzylation of the corresponding hydroxy[3.3]MCPs, which are obtained by demethylation of methoxy[3.3]MCPs with BBr3 at room temperature. An interesting and intriguing result was obtained when syn-6,15-di-tert-butyl-9-methoxy-18-methyl[3.3]MCP-2,11-dione was treated with TMSI to afford the formation of a dihydrobenzofuran ring by a nucleophilic intramolecular cyclization reaction. The 1H NMR and X-ray analysis of 6a confirms that it adopts a syn (chair-chair) conformation in both solution and solid state.

Original languageEnglish
Pages (from-to)1161-1168
Number of pages8
JournalCanadian Journal of Chemistry
Volume93
Issue number11
DOIs
Publication statusPublished - May 26 2015

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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