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Photoinduced Rearrangement of Dienones and Santonin Rerouted by Amines

Zhang, Zhipeng and Ratnikov, Max and Spraggon, Glen and Alper, Phillip (2018) Photoinduced Rearrangement of Dienones and Santonin Rerouted by Amines. Angewandte Chemie. International edition, 57 (4). pp. 904-908. ISSN 14337851

Abstract

The photoinduced rearrangement pathways of simple 2,5-dienones and the natural product Santonin were found to be effectively rerouted by amines, giving rise to unprecedented products. Either cis olefins or cyclobutenes were obtained from 4,4-disubstituted 2,5-dienone upon irradiation (365 nm) in the presence of various amines depending on the solvent. Previously undescribed [4,4,0] and [5,3,0] fused ring containing products were obtained when Santonin was irradiated (365 nm) in the presence of methylamine. The amines present in these reactions were incorporated into the products via amide group formation.

Item Type: Article
Date Deposited: 27 Mar 2018 00:45
Last Modified: 27 Mar 2018 00:45
URI: https://oak.novartis.com/id/eprint/35098

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