Syntheses of 6,7-Benzotropolones by a Sequence of Acylation (or α-Hydroxyalkylation/Oxidation), Ring-Closing Metathesis, and Hydrolysis/β-Elimination
Starting from ortho-bromostyrenes, 12 6,7-benzotropolones were synthesized in 3 or 4 steps. Br/Li exchanges provided the respective ortho-lithiostyrenes. The latter were acylated by a Weinreb amide, if unhindered, or hydroxyalkylated by an aldehyde, if hindered (an oxidation ensuing thereafter). Acetonide-containing benzannulated nonatrienones resulted. Ring-closing olefin metatheses converted them into acetonide-containing benzocycloheptadienones. Treatment with aq. HCl caused hydrolyses followed by β-elimination reactions giving 6,7-benzotropolones.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:87 |
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| Enthalten in: |
The Journal of organic chemistry - 87(2022), 22 vom: 18. Nov., Seite 15415-15420 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Momm, Sarah N [VerfasserIn] |
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| Links: |
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| Themen: |
Alkenes |
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| Anmerkungen: |
Date Completed 21.11.2022 Date Revised 06.01.2023 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.joc.2c01968 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM348327714 |
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| 245 | 1 | 0 | |a Syntheses of 6,7-Benzotropolones by a Sequence of Acylation (or α-Hydroxyalkylation/Oxidation), Ring-Closing Metathesis, and Hydrolysis/β-Elimination |
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| 500 | |a Date Completed 21.11.2022 | ||
| 500 | |a Date Revised 06.01.2023 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Starting from ortho-bromostyrenes, 12 6,7-benzotropolones were synthesized in 3 or 4 steps. Br/Li exchanges provided the respective ortho-lithiostyrenes. The latter were acylated by a Weinreb amide, if unhindered, or hydroxyalkylated by an aldehyde, if hindered (an oxidation ensuing thereafter). Acetonide-containing benzannulated nonatrienones resulted. Ring-closing olefin metatheses converted them into acetonide-containing benzocycloheptadienones. Treatment with aq. HCl caused hydrolyses followed by β-elimination reactions giving 6,7-benzotropolones | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
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