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1. Photoinduced [4 + 4], [4 + 2], and [2 + 2] cycloadditions of o-quinones with oxazoles: chemo-, regio-, and diastereoselectivity

Author

Lei Wang, Yu-Cheng Huang, Yang Liu, Hoong-Kun Fun, Yan Zhang, and Jian-Hua Xu

Subjects
Carbonyl compounds -- Structure, Carbonyl compounds -- Chemical properties, Carbonyl compounds -- Optical properties, Ring formation (Chemistry) -- Analysis, Oxazoles -- Structure, Oxazoles -- Chemical properties, Quinone -- Structure, Quinone -- Chemical properties, Biological sciences, Chemistry
Abstract

The studies about the photoinduced reactions of the 1,2-dicarbonyl compounds phenanthrenequinone (PQ), 1-acetylisatin (IS) and benzil (BZ) with the oxazoles are discussed. Regio- and diastereoselectivity in the [2 + 2] and [4 + 4] cycloadditions based on the thermodynamic stability of the relevant triplet diradical intermediates and the conformations of these diradicals suitable for the intersystem crossing process are also discussed.

Published
2010

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