Travnicek, Martin and Potacek, Milan and Mannschreck, Albrecht (2001) Stereochemistry of 1,3-dipolar cycloaddition reaction of azomethine ylides derived from N-alkyl-N-(4-toluenesulphonyl) carbamoylmethyl phenanthridinium with olefinic dipolarophiles. HETEROCYCLIC COMMUNICATIONS, 7 (3). pp. 213-222. ISSN 0793-0283
Full text not available from this repository. (Request a copy)Abstract
A series of prepared N-alkyl-N-(p-toluenesulphonyl) bromoacetamides 1a-1b afforded with phenanthridine quaternary phenanthridinium salts 2a-2b. These, when treated with triethylamine in dichloromethane, form azomethine ylides that udergo cycloaddition reaction with present activated olefinic C=C double bond. This way pyrrolidino[1,2-f] phenanthridines 3-5 can be obtained. Their stereochemistry was studied by means of NMR spectroscopy. This family of phenanthridinium based ylides reacts very willingly with common olefinic dipolarophiles (dimethyl fumarate, dimethyl maleate or fumaronitrile) more or less stereoselectively. Some of the prepared racemic cycloadducts 3-5 were separated by HPLC on non-racemic cellulose-based sorbents with CD detection.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HETEROAROMATIC N-YLIDES; CYCLO-ADDITION REACTIONS; LIQUID-CHROMATOGRAPHY; ACRYLOYL; SULTAM; |
| 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: | 28 Feb 2022 14:15 |
| Last Modified: | 28 Feb 2022 14:15 |
| URI: | https://pred.uni-regensburg.de/id/eprint/41866 |
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