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http://nopr.niscpr.res.in/handle/123456789/16237| Title: | A type 1 intramolecular Diels-Alder approach to the mniopetals: Intervention of a thennal [1,5] hydrogen shift |
| Authors: | Allen(Jr), Aberdeen Gordon, Dana M |
| Issue Date: | Mar-1999 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | An approach to mniopetals A-F (1-6) based on a type 1 intramolecular Diels-Alder (IMDA) reaction has been investigated. The substrate 12 for the envisioned IMDA reaction is either unreactive or decomposes upon exposure to Lewis acids over a range of temperatures; heating a solution of 12 in toluene at 110 °C, however, produces itaconate 14 in 80% yield. The stereospecific formation of 14 from 12 can be rationalized by a thermal [1,5] hydrogen shift. Analogously, thermolysis of alkenyl maleates 15a-c at 110 °C in toluene or 1,2-dibromoethane gives good yields of itaconates 16a-c, respectively. |
| Page(s): | 269-273 |
| Appears in Collections: | IJC-B Vol.38B(03) [March 1999] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 38B(3) 269-273.pdf | 1.19 MB | Adobe PDF | View/Open |
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