Contrasting Behaviour of Exciplex Ensembles in the Diastereodifferentiating Paternò–Büchi Reaction of Chiral Cyanobenzoate with Naphthyl- and Phenylethenes on Direct or Charge-Transfer Excitation
Keisuke Nagasaki A , Yoshihisa Inoue A and Tadashi Mori A B
+ Author Affiliations
- Author Affiliations
A Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan.
B Corresponding author. Email: tmori@chem.eng.osaka-u.ac.jp
Australian Journal of Chemistry 68(11) 1693-1699 https://doi.org/10.1071/CH15404
Submitted: 6 July 2015 Accepted: 19 July 2015 Published: 7 August 2015
Abstract
The diastereodifferentiating Paternò–Büchi reaction of chiral cyanobenzoate with 1-(1-naphthyl)-1-phenylethene was compared with those with 1,1-diphenylethene on direct and charge-transfer excitations. By desymmetrization of the donor, four diastereomeric oxetane products were formed on photolysis in excellent combined yields. Increase in donor strength induced a stronger charge-transfer interaction both in ground and excited states. Thus, the difference in diastereoselectivities with two different excitation modes (i.e. direct versus charge-transfer) became less significant with a naphthyl derivative as donor. A subtle change of donor–acceptor interaction was shown to have profound effect on the nature of the excited-state complexes and thus the product (stereo)selectivities. Despite a small temperature dependence, an Eyring-type study on the diastereoselectivities confirmed that the excited charge-transfer complex is an excited species distinct from the conventional exciplex.
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