Abstract
Under mechanochemical milling conditions, Diels-Alder
cycloaddition of cyclopentadiene with maleic anhydride and maleimide
derivatives proceeded very smoothly, affording endo -norbornenes
exclusively in quantitative yield. All the transformations were
accomplished at room temperature without using any catalyst or organic
solvent, thus the workup and purification procedure is very simple.
Control experiments on traditional and other tentative conditions
were also investigated.
Key words
norbornenes - mechanochemical milling - solvent-free - cyclopentadiene - Diels-Alder
reaction
References and Notes
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Analytical Data
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Mp 156-157 ˚C. IR (KBr): 2954,
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NMR (400 MHz, CDCl3 ): δ = 1.59 (d, J = 8.8 Hz,
1 H), 1.78 (d, J = 8.8
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