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 journalArticle

4 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 - Jan 1 2017

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Alkanes
epoxy compounds
Epoxy Compounds
Cyclization
Conformations
Carbon
X-Rays
Acids
X ray analysis
synthesis
products
Discrete Fourier transforms
Single crystals
methylene
alkanes
acids
carbon
single crystals
estimates
x rays

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes. / Akther, Thamina; Islam, Md Monarul; Rahman, Shofiur; Georghiou, Paris E.; Matsumoto, Taisuke; Tanaka, Junji; Redshaw, Carl; Yamato, Takehiko.

In: Organic and Biomolecular Chemistry, Vol. 15, No. 16, 01.01.2017, p. 3519-3527.

Research output: Contribution to journalArticle

Akther, T, Islam, MM, Rahman, S, Georghiou, PE, Matsumoto, T, Tanaka, J, Redshaw, C & Yamato, T 2017, 'Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes', Organic and Biomolecular Chemistry, vol. 15, no. 16, pp. 3519-3527. https://doi.org/10.1039/c7ob00400a
Akther, Thamina ; Islam, Md Monarul ; Rahman, Shofiur ; Georghiou, Paris E. ; Matsumoto, Taisuke ; Tanaka, Junji ; Redshaw, Carl ; Yamato, Takehiko. / Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes. In: Organic and Biomolecular Chemistry. 2017 ; Vol. 15, No. 16. pp. 3519-3527.
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AU - Georghiou, Paris E.

AU - Matsumoto, Taisuke

AU - Tanaka, Junji

AU - Redshaw, Carl

AU - Yamato, Takehiko

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AB - 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.

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