Journal
CANADIAN JOURNAL OF CHEMISTRY
Volume 90, Issue 5, Pages 441-449Publisher
CANADIAN SCIENCE PUBLISHING
DOI: 10.1139/V2012-014
Keywords
metacyclophan-1-ene; dehydrobromination; metacyclophan-1-yne; double intramolecular cyclization; benzofuranophane
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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.
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