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Indexed by:期刊论文

Date of Publication:2014-01-01

Journal:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Included Journals:SCIE、Scopus

Volume:2014

Issue:3

Page Number:515-522

ISSN No.:1434-193X

Key Words:Synthetic methods; Polyenes; Ketones; Dimerization; Reduction

Abstract:A strategy for the stereoselective synthesis of (2Z,4Z,6Z,8Z)-decatetraene diketone by the one-step metal reduction of pyrylium salts is described. Reduction of -active pyrylium salts (at least one H at the -C positon) leads to only linear decatetraene diketone derivatives, whereas reduction of -non-active pyrylium salts (no H at the -C position) generates two unexpected structures and one linear decatetraene diketone. The reaction conditions were optimized, and a reaction mechanism was proposed. Single-crystal structures of decatetraene diketone derivatives demonstrate the twisted configuration of the backbones and the all-(Z) geometry of the double bonds. In addition, the thermal, optical, and electrochemical properties of these compounds were studied in detail.