Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes

Thamina Akther, Md Monarul Islam, Shofiur Rahman, Paris E. Georghiou, Taisuke Matsumoto, Junji Tanaka, Carl Redshaw, Takehiko Yamato

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A series of syn- and anti-[2.n]metacyclophan-1-enes have been prepared in good yields by McMurry cyclizations of 1,n-bis(5-tert-butyl-3-formyl-2-methoxyphenyl)alkanes. Significantly, acid catalyzed rearrangements of [2.n]metacyclophan-1-enes afforded [n.1]metacyclophanes in good yield. The ratios of the products are strongly regulated by the number of methylene bridges present. The percentages of the rearrangement products increase with increasing length of the carbon bridges. Characterization and the conformational studies of these products are described. Single crystal X-ray analysis revealed the adoption of syn- and anti-conformations. DFT calculations were carried out to estimate the energy-minimized structures of the synthesized metacyclophanes.

Original languageEnglish
Pages (from-to)3519-3527
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number16
DOIs
Publication statusPublished - 2017

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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