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One‐Step Stereoselective Synthesis of (2 Z, 4 Z, 6 Z, 8 Z )‐Decatetraene Diketone from Pyrylium Salts
Author(s) -
Yang Lijian,
Ye Junwei,
Gao Yuan,
Deng Dai,
Lin Yuan,
Ning Guiling
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301685
Subject(s) - diketone , chemistry , stereoselectivity , stereochemistry , metal , medicinal chemistry , organic chemistry , catalysis
A strategy for the stereoselective synthesis of (2 Z ,4 Z ,6 Z ,8 Z )‐decatetraene diketone by the one‐step metal reduction of pyrylium salts is described. Reduction of α‐active pyrylium salts (at least one H at the α‐C positon) leads to only linear decatetraene diketone derivatives, whereas reduction of α‐non‐active pyrylium salts (no H at the α‐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.