Details
| Original language | English |
|---|---|
| Pages (from-to) | 4877-4884 |
| Number of pages | 8 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 25 |
| Publication status | Published - 8 Jul 2011 |
Abstract
Treatment of 1,4-dibromo-2,5-dimethoxybenzene (6) with NaNH2 followed by 1,1-dimethoxyethene (7) afforded the bi- and tricyclic acetals such as 8 and 9 as the products of [2+2] cycloadditions of the intermediate arynes. After chromatographic separation and acetal hydrolysis the title compounds 15 and 16 were obtained in high yields as the first representatives of their class. Complexation of the acetals with Cr(CO)6 gave the corresponding tricarbonylchromium complexes in excellent yields. Subsequent deacetalization afforded the diketone complexes 18 and rac-20, which underwent stereoselective nucleophilic diadditions at -78 °C.
Keywords
- Arynes, Chromium, Fused-ring systems, Polycycles, Regioselectivity, Small ring systems
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, No. 25, 08.07.2011, p. 4877-4884.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The first benzo[1,2:4,5]dicyclobutenones and their tricarbonylchromium complexes
AU - Abdelhamid, Ismail Abdelshafy
AU - Habib, Osama Mahmoud Ali
AU - Butenschön, Holger
PY - 2011/7/8
Y1 - 2011/7/8
N2 - Treatment of 1,4-dibromo-2,5-dimethoxybenzene (6) with NaNH2 followed by 1,1-dimethoxyethene (7) afforded the bi- and tricyclic acetals such as 8 and 9 as the products of [2+2] cycloadditions of the intermediate arynes. After chromatographic separation and acetal hydrolysis the title compounds 15 and 16 were obtained in high yields as the first representatives of their class. Complexation of the acetals with Cr(CO)6 gave the corresponding tricarbonylchromium complexes in excellent yields. Subsequent deacetalization afforded the diketone complexes 18 and rac-20, which underwent stereoselective nucleophilic diadditions at -78 °C.
AB - Treatment of 1,4-dibromo-2,5-dimethoxybenzene (6) with NaNH2 followed by 1,1-dimethoxyethene (7) afforded the bi- and tricyclic acetals such as 8 and 9 as the products of [2+2] cycloadditions of the intermediate arynes. After chromatographic separation and acetal hydrolysis the title compounds 15 and 16 were obtained in high yields as the first representatives of their class. Complexation of the acetals with Cr(CO)6 gave the corresponding tricarbonylchromium complexes in excellent yields. Subsequent deacetalization afforded the diketone complexes 18 and rac-20, which underwent stereoselective nucleophilic diadditions at -78 °C.
KW - Arynes
KW - Chromium
KW - Fused-ring systems
KW - Polycycles
KW - Regioselectivity
KW - Small ring systems
UR - http://www.scopus.com/inward/record.url?scp=80051990339&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201100551
DO - 10.1002/ejoc.201100551
M3 - Article
AN - SCOPUS:80051990339
SP - 4877
EP - 4884
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 25
ER -