Publication details
Stereoselective 1,3-dipolar cycloaddition of a nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine to substituted methylene lactones
| Authors | |
|---|---|
| Year of publication | 2000 |
| Type | Article in Periodical |
| Magazine / Source | Collection of Czechoslovak Chemical Communications |
| MU Faculty or unit | |
| Citation | |
| Web | http://cccc.uochb.cas.cz/ |
| Field | Organic chemistry |
| Keywords | methylene lactones; nitrile ylide; dipolar cycloaddition; spiro compounds; regioselectivity; stereoselectivity |
| Description | The nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine adds to both isomers of 3-(tosyloxymethylene)tetrahydrofuran-2-one with excellent regio- and stereoselectivity giving spiroheterocyclic products in moderate yields. X-Ray structure determination showed dibutolactone to have the E-configuration. The corresponding Z-isomer was prepared photochemically. |
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