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Effect of Ring Size on the Exo/Endo Selectivity of a Thermal Double Cycloaddition of Fused Pyran-2-ones

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journal contribution
posted on 21.08.2009, 00:00 by Kris̆tof Kranjc, Franc Perdih, Marijan Koc̆evar
A study of an unusual effect of the size of the ring fused to 2H-pyran-2-ones on the exo/endo selectivity of a thermal double cycloaddition of N-substituted maleimides or maleic anhydride yielding bicyclo[2.2.2]octene derivatives is presented. With subtle variations of starting compounds and reaction conditions exclusively exo,exo or exo,endo products can be prepared.