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Cyclobutenone was employed as a dienophile in Diels-Alder cycloadditions, provide diverse and complex cycloadducts in good yields. Experimental outcomes indicated cyclobutenone to be more reactive than either cyclopentenone or cyclohexenone. In addition, cycloadducts bearing a strained cyclobutanone moiety were able to undergo regioselective ring expansions to produce corresponding cyclopentanones, lactones, and lactams, which are otherwise difficultly obtained by direct Diels-Alder reactions.

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Halocycloalkenones as DielsAlder Dienophiles. Applications to Generating Useful Structural PatternsRoss, A. G.; Townsend, S. D.; Danishefsky, S. J. J. Org. Chem. ASAP Nov. 14 2012As promised, I have a review for today, the last one of 2012! I was all set to...
Halocycloalkenones as DielsAlder Dienophiles. Applications to Generating Useful Structural PatternsRoss, A. G.; Townsend, S. D.; Danishefsky, S. J. J. Org. Chem. ASAP Nov. 14 2012As promised, I have a review for today, the last one of 2012! I was all set to...
Li and Danishefsky report a study of the Diels-Alder reaction involving cyclobutenone 1 as the dienophile.1 They claim that perhaps the ring strain of 1 might well serve to enhance its dienophilicity relative to corresponding cyclopentenones or cyclohexenones....