Synthesis of crossed [2 + 2] photocycloadducts: a novel approach to the synthesis of bridged bicyclic alkenes.
[reaction: see text] A solution to the synthesis of "crossed" intramolecular [2 + 2] photocycloadducts has been achieved. Through the use of a temporary heteroatom linker, the equivalent of a crossed photocycloadduct can be accessed at the expensive of the normal "straight" adduct. Selectivity as high as 94:6 for the "crossed" adduct has been observed.
Crimmins
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MT
Venable and Kenan Laboratories of Chemistry, The University of North Carolina at Chapel Hill, 27599-3290, USA. crimmins@email.unc.edu
Hauser
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EB
D000475:Alkenes / Q000138:chemical synthesis; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D010777:Photochemistry
D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds