Intramolecular photocycloaddition of dioxenones with alkynes: formation of secondary photoproducts from cyclobutene photoadducts.
[Reaction: see text] Intramolecular photocycloaddition of 4 leads to the formation of cyclobutene photoadduct 5. Secondary photoreaction of 5 then affords either cyclobutane 19 or the bridged product 7, as a function of R (H or TMS).
Winkler
Jeffrey D
JD
Department of Chemistry, The University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. winkler@sas.upenn.edu
McLaughlin
Emily C
EC
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D004146:Dioxanes / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry
D000475:Alkenes; D000480:Alkynes; D003503:Cyclobutanes; D004146:Dioxanes; D006575:Heterocyclic Compounds, 3-Ring