Photochemical Studies on Benzonorbornene Derivatives: Medium Effects and Asymmetric Induction

Title: Photochemical Studies on Benzonorbornene Derivatives: Medium Effects and Asymmetric Induction

Volume: 6 Issue: 1

Author(s): Chao Yang, Wujiong Xia, Qian Chen, Xiao Zhang, Bing Li and Baoquan Gou

Affiliation:

Keywords: Benzonorbornene, solid state, Norrish type II, enantiomeric excesses, asymmetric synthesis

Abstract: The photochemical behaviors of benzonorbornene derivatives were investigated in the solid state as well as in the solution. In acetonitrile solution, benzonorbornene derivatives underwent the Norrish type II reaction affording a ratio of 1:1 of cyclization and cleavage products, whereas in the solid state, the sole cyclization product was obtained. The stereochemistry of the photoproducts was identified by the X-ray crystallography. Enantiomeric excesses of up to 97% can be achieved through the use of the solid-state ionic chiral auxiliary method of asymmetric synthesis.

Cite this article as:

Yang Chao, Xia Wujiong, Chen Qian, Zhang Xiao, Li Bing and Gou Baoquan, Photochemical Studies on Benzonorbornene Derivatives: Medium Effects and Asymmetric Induction, Letters in Organic Chemistry 2009; 6 (1) . https://dx.doi.org/10.2174/157017809787003098