Rochlin, Elimelech and Rappoport, Zvi and Kastner, Fritz and Pustet, Nikola and Mannschreck, Albrecht (1999) Four enantiomerization routes of 1,2,2-trimesitylvinyl acetate. Enantioselective liquid chromatography of (E)- and (Z)-2-m-methoxymesityl-1,2-dimesitylvinyl acetates. JOURNAL OF ORGANIC CHEMISTRY, 64 (24). pp. 8840-8845. ISSN 0022-3263,
Full text not available from this repository.Abstract
The vinyl propellers (E)- End (Z)-2-m-methoxymesityl-1,2-dimesitylvinyl acetates (3c and 3d) were prepared and their geometries assigned. The stereoisomerization barriers of the trimesityl vinyl acetate system were determined by DNMR and by enantioselective LC resolution and polarimetric monitoring of the behavior of the two diastereomeric racemates of Sc and Sd. Combined with data for trimesitylvinyl-OAc 3a and its 1-m-methoxymesityl analogue 3b, the following order of barriers Delta G double dagger is obtained: alpha beta-2-ring flip > alpha beta'-2-ring flip > beta beta'-2-ring flip, alpha beta beta'-3-ring flip (the threshold enantiomerization barrier). This order which differs from the previously found orders for trimesitylvinyl-X, X = H, OPr-i was rationalized and discussed.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CIRCULAR-DICHROISM SPECTRA; STABLE SIMPLE ENOLS; TRIARYLVINYL PROPELLERS; ONLINE MEASUREMENT; 3-RING FLIP; BARRIERS; STEREOCHEMISTRY; RESOLUTION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Prof.Dr. Mannschreck |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 06 Dec 2022 14:29 |
| Last Modified: | 06 Dec 2022 14:29 |
| URI: | https://pred.uni-regensburg.de/id/eprint/48824 |
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