Synthesis and properties of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone
The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2?-chloroethoxy)ethane, two units derived from isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), 7,7,12,12-tetramet...
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| Hauptverfasser: | , , , |
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| Dokumenttyp: | Article (Journal) Festschrift |
| Sprache: | Englisch |
| Veröffentlicht: |
12 May 1999
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| In: |
European journal of organic chemistry
Year: 1999, Heft: 6, Pages: 1303-1310 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/(SICI)1099-0690(199906)1999:6<1303::AID-EJOC1303>3.0.CO;2-M |
| Schlagworte: | |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/(SICI)1099-0690(199906)1999:6<1303::AID-EJOC1303>3.0.CO;2-M Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/%28SICI%291099-0690%28199906%291999%3A6%3C1303%3A%3AAID-EJOC1303%3E3.0.CO%3B2-M 
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| Verfasserangaben: | Christoph Braunweiler, Sabine Bethke, Frank Rominger, and Rolf Gleiter |
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| 245 | 1 | 0 | |a Synthesis and properties of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone |c Christoph Braunweiler, Sabine Bethke, Frank Rominger, and Rolf Gleiter |
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| 500 | |a Dedicated to Professor Werner Tochtermann on the occasion of his 65th birthday | ||
| 500 | |a Gesehen am 22.10.2020 | ||
| 520 | |a The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2?-chloroethoxy)ethane, two units derived from isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), 7,7,12,12-tetramethyl-1,4-dioxa-9-cyclotetradecyne-2,8-diolprotected by one tetrahydropyran group (15), and 8,11-dihydroxy-7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-9,10-dione (18). X-ray investigation on single crystals of the (R,S) isomer 18a revealed a transannular interaction between the dioxaethane bridge and the dicarbonyl moiety. Calculations (HF/6-31G*) on 4 predict relatively short distances between the oxygen atoms of the dioxyethane bridge and the (CO)4 part. Investigations by means of cyclic voltammetry, PE and UV/Vis spectroscopy on 4 reveal an interaction between the dioxaethane bridge and the (CO)4 group. | ||
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