2,2-Dimethylcyclopent-4-ene-1,3-dione (1) is a poor dienophile but a normally active 1,3-dipolarophile; these observations imply that the orientation of addends in reaction of 1,3-dipoles with (1) is that shown in (8) and not (9).
W. C. Agosta and A. B. Smith, J. Chem. Soc. D, 1970, 685b DOI: 10.1039/C2970000685B
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