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 language | English |
|---|---|
| Pages (from-to) | 441-449 |
| Number of pages | 9 |
| Journal | Canadian Journal of Chemistry |
| Volume | 90 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - May 1 2012 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Organic Chemistry
Cite this
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 journal › Article
}
TY - JOUR
T1 - 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
AU - Uchikawa, Yuki
AU - Tazoe, Kazuya
AU - Tanaka, Syogo
AU - Feng, Xing
AU - Matsumoto, Taisuke
AU - Tanaka, Junji
AU - Yamato, Takehiko
PY - 2012/5/1
Y1 - 2012/5/1
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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U2 - 10.1139/v2012-014
DO - 10.1139/v2012-014
M3 - Article
AN - SCOPUS:84860533924
VL - 90
SP - 441
EP - 449
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
SN - 0008-4042
IS - 5
ER -