Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2014-01-01

Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Included Journals: Scopus、SCIE

Volume: 2014

Issue: 3

Page Number: 515-522

ISSN: 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.