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

doi:10.1039/c7ob00400a

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

Department of Fundamental Organic Chemistry

Research output: Contribution to journal › Article › peer-review

7 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 language	English
Pages (from-to)	3519-3527
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	16
DOIs	https://doi.org/10.1039/c7ob00400a
Publication status	Published - 2017

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

author = "Thamina Akther and Islam, {Md Monarul} and Shofiur Rahman and Georghiou, {Paris E.} and Taisuke Matsumoto and Junji Tanaka and Carl Redshaw and Takehiko Yamato",

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doi = "10.1039/c7ob00400a",

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pages = "3519--3527",

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T1 - Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes

AU - Akther, Thamina

AU - Islam, Md Monarul

AU - Rahman, Shofiur

AU - Georghiou, Paris E.

AU - Matsumoto, Taisuke

AU - Tanaka, Junji

AU - Redshaw, Carl

AU - Yamato, Takehiko

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - 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.

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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DO - 10.1039/c7ob00400a

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SN - 1477-0520

VL - 15

SP - 3519

EP - 3527

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 16

ER -

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

Abstract

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