1515-21-5Relevant articles and documents
Structural studies on α-pyrone cycloadducts. Manifestation of the early stages of CO2 extrusion by retro hetero-DielsAlder reaction
Roth-Barton, Jesse,Goh, Yit Wooi,Karnezis, Asimo,White, Jonathan M.
, p. 407 - 412 (2009)
Structures of the -pyrone (pyran-2-one) cycloadducts 48 show deviations of some bond distances from their normal values, consistent with manifestation of the early stages of the retro hetero-DielsAlder decarboxylation reaction in the ground state structures. Thus the bridgehead CO(CO) and CCO(O) bonds are lengthened and the bridging CO bond is shortened. The degree of lengthening of the CO(CO) and CCO(O) bonds is similar, whereas in the calculated transition state structure there is significant asymmetry in the extent of CCO(O) and CO(CO) bond breaking. CSIRO 2009.
Synthesis of Some 3-Oxo-2-oxabicyclooct-7-ene Derivatives and Attempts of their Conversion into 3-Oxo-2-oxabicycloocta-5,7-diene
Pfaff, Eberhard,Plieninger, Hans
, p. 1967 - 1981 (2007/10/02)
Acryloyl chloride, 2-chloroacrylonitrile, and fumaric ethyl ester chloride react at high pressure (5-10 kbar) with 2H-pyran-2-one to give 1:1 adducts.With maleic anhydride and fumaroyl dichloride purer products in higher yields are obtained at high pressure.The constitution and configuration of the products are determined in most cases.Starting with these compounds we have synthesized a large number of 3-oxo-2-oxabicyclooct-7-ene derivatives.Elimination experiments lead to the conclusion that 3-oxo-2-oxabicycloocta-5,7-diene (I) is not stable above 0 deg C.
