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Theory of Substituent Effects on the Regioselectivity of Di-π-methane Rearrangements of Dibenzobarrelenes

✍ Scribed by Matute, Ricardo A.; Garcia-Garibay, Miguel A.; Houk, K. N.


Book ID
126884937
Publisher
American Chemical Society
Year
2014
Tongue
English
Weight
278 KB
Volume
16
Category
Article
ISSN
1523-7060

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Substituent effect on regioselectivity i
✍ Nermin S Ünaldi; Metin Balci 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 65 KB

2,3-and 2,5-Dicyanobenzobarrelenes 5 and 6 have been synthesized and subjected to triplet-sensitized photoisomerization. 2,3-Dicyanobenzobarrelene 5 gave two di-p-methane rearrangement products 7 and 8 and a [2p+2p]-cycloaddition product 9. However, 2,5-dicyanobenzobarrelene 6 formed a single di-p-m