Structures of oxygenated cyclohexa-1,3-diene-maleic anyhydride cycloadducts. Structural evidence suggests a stepwise retro-Diels-Alder reaction.
The structures of a series of cyclohexadiene-maleic anhydride cycloadducts show structural parameters consistent with the early stages of the retro-Diels-Alder (rDA) reaction in the ground state structure. The symmetrical adduct shows effects consistent with a synchronous rDA reaction. An asynchronous rDA reaction is suggested in the structure of 8, and the first evidence suggesting a two-step retro-Diels-Alder mechanism is provided by the deoxygenated adduct 9.
Goh
Yit Wooi
YW
School of Chemistry and Bio-21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia.
White
Jonathan M
JM