engleski

Parity reversal: A new Diels-Alder strategy for the synthesis of sesquinorbornadienes, including those with heterobridges and those of unusual stereochemistry

The concept of parity reversal, where interchange of the substituent at the 5-position of a cyclic 5-membered 1,3-diene with the substituent at the 7-position of a norbornadiene anhydride, provides two sets of Diels-Alder reagents which each yield mixtures of ext-face adducts, one member of which always corresponds to the rare endo-face adduct of the parity reversal combination. AM1, nb initio and higher order calculations of TS energies are used to predict outcomes.

Diels-Alder cycloaddition; norbornadiene anhydrides; endo-adducts; hetero-bridged sesquinorbornadienes; AM1; ab initio

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