Synthesis and demethylation of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr 3 to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11- bromochromenophane

Yuki Uchikawa, Kazuya Tazoe, Syogo Tanaka, Xing Feng, Taisuke Matsumoto, Junji Tanaka, Takehiko Yamato

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

4,22-Dimethoxy[2.10]metacyclophan-1-yne was prepared by bromination of [2.10]metacyclophan-1-ene followed by the dehydrobromination of the bromine adduct with KOBu-t. Treatment of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr 3 in CH 2Cl 2 at room temperature led to the demethylation and a successive intramolecular cyclization reaction to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11-bromochromenophane in good yield. Similar treatment of a mixture of the corresponding meso-and dl-1,2-dibromo-4,22-dimethoxy[2.10]metacyclophane with BBr 3 in CH 2Cl 2 under the same conditions described above afforded cis-4b,9b-dihydro[10]benzofuro[3,2-b]benzofuranophane in 83% yield.

Original languageEnglish
Pages (from-to)441-449
Number of pages9
JournalCanadian Journal of Chemistry
Volume90
Issue number5
DOIs
Publication statusPublished - May 1 2012

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Bromine
Cyclization
Temperature

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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Synthesis and demethylation of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr 3 to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11- bromochromenophane. / Uchikawa, Yuki; Tazoe, Kazuya; Tanaka, Syogo; Feng, Xing; Matsumoto, Taisuke; Tanaka, Junji; Yamato, Takehiko.

In: Canadian Journal of Chemistry, Vol. 90, No. 5, 01.05.2012, p. 441-449.

Research output: Contribution to journalArticle

Uchikawa, Yuki ; Tazoe, Kazuya ; Tanaka, Syogo ; Feng, Xing ; Matsumoto, Taisuke ; Tanaka, Junji ; Yamato, Takehiko. / Synthesis and demethylation of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr 3 to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11- bromochromenophane. In: Canadian Journal of Chemistry. 2012 ; Vol. 90, No. 5. pp. 441-449.
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abstract = "4,22-Dimethoxy[2.10]metacyclophan-1-yne was prepared by bromination of [2.10]metacyclophan-1-ene followed by the dehydrobromination of the bromine adduct with KOBu-t. Treatment of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr 3 in CH 2Cl 2 at room temperature led to the demethylation and a successive intramolecular cyclization reaction to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11-bromochromenophane in good yield. Similar treatment of a mixture of the corresponding meso-and dl-1,2-dibromo-4,22-dimethoxy[2.10]metacyclophane with BBr 3 in CH 2Cl 2 under the same conditions described above afforded cis-4b,9b-dihydro[10]benzofuro[3,2-b]benzofuranophane in 83{\%} yield.",
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N2 - 4,22-Dimethoxy[2.10]metacyclophan-1-yne was prepared by bromination of [2.10]metacyclophan-1-ene followed by the dehydrobromination of the bromine adduct with KOBu-t. Treatment of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr 3 in CH 2Cl 2 at room temperature led to the demethylation and a successive intramolecular cyclization reaction to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11-bromochromenophane in good yield. Similar treatment of a mixture of the corresponding meso-and dl-1,2-dibromo-4,22-dimethoxy[2.10]metacyclophane with BBr 3 in CH 2Cl 2 under the same conditions described above afforded cis-4b,9b-dihydro[10]benzofuro[3,2-b]benzofuranophane in 83% yield.

AB - 4,22-Dimethoxy[2.10]metacyclophan-1-yne was prepared by bromination of [2.10]metacyclophan-1-ene followed by the dehydrobromination of the bromine adduct with KOBu-t. Treatment of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr 3 in CH 2Cl 2 at room temperature led to the demethylation and a successive intramolecular cyclization reaction to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11-bromochromenophane in good yield. Similar treatment of a mixture of the corresponding meso-and dl-1,2-dibromo-4,22-dimethoxy[2.10]metacyclophane with BBr 3 in CH 2Cl 2 under the same conditions described above afforded cis-4b,9b-dihydro[10]benzofuro[3,2-b]benzofuranophane in 83% yield.

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