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- Title
Synthesis and conformational studies of 9-benzyloxy-18-substituted [3.3]metacyclophanes.
- Authors
Islam, M. Monarul; Hirotsugu, Tomiyasu; Matsumoto, Taisuke; Tanaka, Junji; Yamato, Takehiko
- 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.
- Subjects
CYCLOPHANES synthesis; DEMETHYLATION; SUBSTITUENTS (Chemistry); WOLFF-Kishner reduction; COUPLING reactions (Chemistry)
- Publication
Canadian Journal of Chemistry, 2015, Vol 93, Issue 11, p1161
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2015-0174