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
Y1 - 2012/5
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 -