84507-41-5Relevant articles and documents
Diels-Alder Reactions with 2H-Pyran-2-ones: Reactivity and Selectivity
Effenberger, Franz,Ziegler, Thomas
, p. 1339 - 1346 (2007/10/02)
2H-Pyran-2-ones 1 react with maleic anhydride (2) in a double Diels-Alder reaction to give bicyclooct-2-ene-5,6:7,8-tetracarboxylic dianhydrides 5; the syn/syn structure was established.As expected, the reactivity of 1 was increased by electron donor substituents (OR, alkyl) and diminished by electron withdrawing substituents (CO2R).The steric influence of substituents at C-6 also decrease the reactivity of 1. - Methyl propiolate (6) and phenylacetylene (9) react with 1 to form the Diels-Alder products 7 which suffer CO2 elimination to yield methyl benzoates 8 with low and biphenyls 10 with high regioselectivity, respectively.