Breu, Josef and Range, Klaus-Jürgen and Weber, Andreas and Sauer, Jürgen (1998) Nonstereospecific 1,3-dipolar cycloaddition reactions of azomethine ylides: Proof of the structures for four diastereoisomeric [3+2] cycloadducts. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, C54 (4). pp. 509-513. ISSN 0108-2701, 1600-5759
Full text not available from this repository. (Request a copy)Abstract
Racemic azomethine ylides [(I) or (IV)] have been found to undergo cycloaddition to a trans-enamine [(II)] in a nonstereospecific way to yield mixtures of racemic diastereoisomeric 1:1 adducts: 5-dimethylamino-1,1,6-trimethyl-2,6a-di-p-tolyl-1,1a,5,6,6a,6b-hexahydro-4H-3,3a-diazacyclopropa[e]indene-4,4-dicarbonitrile, C-29-H33N5 [(IIIa) and (IIIb)], or 2-dimethylamino-1,5,5-trimethyl-6-(4-methylbenzoyl)-7a-p-tolyl-2,3,5,7a-tetrahydro-1H-pyrrolizine-3,3-dicarbonitrile (pyrrolizine is pyrrolo[1,2-a]pyrrole), C29H32N4O [(Va) and (Vb)]. Crystal structure analyses prove the structures and configurations for the three diastereoisomeric adducts (ma), (IIIb) and (Vb) unequivocally. In all three cases, the dimethylamino group is endo to the five-membered ring formed in the cycloaddition step. In (cis-1a-cis-4a-transoid-8a,8b-transoid-8b,8c)-1,1-dimethyl-4a-(pyrrolidin-1-yl)-2,8b-di-p-tolyl-1,1a,4a,5,6,7,8,8a,8b,8c-decahydro-4H-3 ,3a-diazacyclopropa[c]fluorene-4,4-dicarbonitrile, C34H39N5, (VII), the cycloadduct formed using an azomethine ylide [(I)] and a cyclic enamine [(VI)], the amino function is again found in an endo position.
| Item Type: | Article |
|---|---|
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 24 Feb 2023 10:52 |
| Last Modified: | 24 Feb 2023 10:52 |
| URI: | https://pred.uni-regensburg.de/id/eprint/49896 |
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