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- Title
Photocycloaddition of Cyclohex-2-enones to Tetramethoxyethylene: Formation of 2,2,3,3-Tetramethoxy-1-oxaspiro[3.5]non-5-enes.
- Authors
Cruciani, Giuliano; Rathjen, Hans-Jürgen; Margaretha, Paul
- Abstract
Cyclohex-2-enones 1a-1c undergo photocycloaddition to tetramethoxyethylene in benzene to afford 1-oxa-spiro[3.5]non-5-enes 3 in very good yields. In MeCN as solvent, higher relative amounts of bicyclo[4.2.0]octan-2-ones 4 are formed. Results from similar experiments with the same enones and 2,3-dimethylbut-2-ene or 1,1-dimethoxyethene indicate that the driving force for oxetane formation is a sufficiently large difference in redox potentials between Ered of the enone and Eox of the alkene. A mechanism is proposed for cycloalk-2-enone + alkene photocycloadditions wherein the cyclobutane adducts arise from an exciplex intermediate and the oxetanes from a subsequently formed contact ion-pair.
- Publication
Helvetica Chimica Acta, 1990, Vol 73, Issue 4, p856
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19900730410