Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 68, Issue 12, Pages 1201-1209Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c20-00590
Keywords
intramolecular Diels-Alder reaction; bridged regioselectivity; medium ring; bicyclo[2.2.2]octane; density functional theory ( DFT) calculation
Funding
- JSPS KAKENHI [JP19K05473]
- Kanazawa University SAKIGAKE project
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Regioselectivity for intramolecular Diels-Alder (IMDA) reactions of 6-acetoxy-6-alkenylcyclohexa-2,4-dien-1-ones that were formed by oxidation of 2-alkenylphenols with lead tetraacetate in acetic acid were studied. Bridged regioselectivity was observed in the IMDA reactions of 6-acetoxy-6-alkenylcyclohexa-2,4-dien-1-ones having a dienophile part which could conjugate with an aromatic group. Bridged seven-and eight-membered rings and bicyclo[2.2.2]octane skeletons were constructed by the present IMDA reactions. Density functional theory (DFT) calculations suggested that conjugation of the dienophile with neighboring aromatic groups lowered the highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energy gap and preceded bridged [4 + 2] adducts.
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