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Aromatic ring-system controls π-facial selectivity in Diels-Alder reactions of [3.3]orthoanthracenophanes

✍ Scribed by Shuntaro Mataka; Jiang Ma; Thies Thiemann; Jerzy M Rudziñski; Tsuyoshi Sawada; Masashi Tashiro


Book ID
103403941
Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
214 KB
Volume
36
Category
Article
ISSN
0040-4039

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Orbital control of π-facial selectivity
✍ Masaru Ishida; Masakazu Sakamoto; Humihiro Hattori; Minako Shimizu; Satoshi Inag 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 193 KB

p-Facial selectivity in Diels-Alder reactions of cyclopentadienes having C( O)YR substituents at the 5-positions was predicted on the basis of the orbital mixing rule and was substantiated experimentally. The selectivity was disclosed to be highly dependent on the relative orbital energy between p H