Photochemical cycloaddition reagents for rigidly attaching the 1, 4-dimethoxynaphthalene chromophore to scaffold alkenes
The norbornanecyclobutene epoxides 1a-1c containing a fused 1, 4-dimethoxynaphthalene chromophore have been reacted with cyclobutenes, cyclohexenes, norbornenes, 7-isopropylidenenorbornenes, 7-azanorbornenes, and other cyclic or electron-deficient alkenes at room temperature to form 1:1 adducts in stereoselective 1,3-dipolar cycloaddition reactions; alkynes can also participate in this reaction. The ability to form 2:1 adducts has also been demonstrated, thereby opening up opportunities for preparing functionalized products with large chromophore separations.
Margetic
D
Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland 4702, Australia, and Centre for Chiral and Molecular Technologies, Deakin University, Geelong, Victoria 3217, Australia.
Russell
RA
Warrener
RN