Retro-Diels-Alder Reaction

Thermal dissociation of Diels-Alder adducts, occurring most readily when one or both fragments are particularly stable:



Early review: H. Kwart, K. King, Chem. Rev. 68, 415-447 (1968). Acceleration by alkoxide substituent: O. Papies, W. Grimme, Tetrahedron Letters 21, 2799 (1980). Application to the synthesis of enethiols: Y. Vallée et al., Synth. Commun. 23, 1267 (1993); of cyclopentadienyl ligands: B. Y. Lee et al., J. Am. Chem. Soc. 116, 2163 (1994). Role in structure elucidation via mass spectrometry: F. Turecek, V. Hanus, Mass Spectrom. Rev. 3, 85-152 (1984). Application to natural product synthesis: A. Ichihara, Synthesis 1987, 207-222; R. W. Sweger, A. W. Czarnik, Comp. Org. Syn. 5, 551-592 (1991).