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- Title
Synthesis and demethylation of 4,22-dimethoxy[2.10]metacyclophan-1-yne with BBr<sub>3</sub> to afford a novel [10](2,9)-5a,11a-benzofuro-5a-bora-11-bromochromenophane.
- Authors
Uchikawa, Yuki; Tazoe, Kazuya; Tanaka, Syogo; Feng, Xing; Matsumoto, Taisuke; Tanaka, Junji; Yamato, Takehiko
- 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 BBr3 in CH2Cl2 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 BBr3 in CH2Cl2 under the same conditions described above afforded cis-4b,9b-dihydro[10]benzofuro[3,2- b]benzofuranophane in 83% yield.
- Subjects
DEMETHYLATION; CYCLOPHANES; DEHYDROBROMINATION; BENZOFURAN; RING formation (Chemistry); TEMPERATURE effect; BROMINE compounds
- Publication
Canadian Journal of Chemistry, 2012, Vol 90, Issue 5, p441
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/v2012-014