ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The VIS-laser irradiation of enol lactones 1a, b and benzoquinone in an argon atmosphere led to the fenestrane-type oxetane 2a and the propellane-type oxetane 2b, with regioselective preference for the acetal structure. Under an oxygen atmosphere both regioisomeric fenestrane-type 1,2,4-trioxanes 4a and 5a were obtained from enol lactone 1a, while no oxygen trapping to the propellane-type trioxanes was observed with 1b. Significant quantities of photooxygenation products were obtained from both enol lactones 1a, b due to singlet oxygen derived from oxygen quenching of benzoquinone triplets. The present study demonstrates that Qinghaosu analoga are accessible via trapping of Paterno-Büchi triplet 1,4-diradicals by molecular oxygen.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19883300309
Permalink