Abstract
Carbonyl Ylides as Cycloaddition Components: Intramolecular Transfer of a DMAD UnitOn heating the specifically designed ene‐oxirane 6 is cleanly transformed into the 2,5‐dihydrofuran derivative 7 As mechanism of this conversion ring opening to carbonyl ylide 8 is proposed followed by formation of the intramolecular cycloadduct 9 which suffers rapid cycloreversion leading to 7. The latter process is precluded in the case of the dihydro derivative 10 which, in fact, reacts under comparable conditions and with equally good yield to give 11 as a thermally stable and sterically pure compound. In the presence of dimethyl acetylene dicarboxylate (DMAD) as external dipolarophile bimolecular cycloadditions do not compete with the intramolecular reaction mode.
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