Chen, Chih-Wei Fan, Kunzeng Chen, Chih-Hsien Huang, Shou-Ling Liu, Yi-Hung Lim, Tsong-Shin Wang, Guan-Wu Luh, Tien-Yau Stereoselective Iterative Convergent Synthesis of <i>Z</i>‑Oligodiacetylenes from Propargylic Dithioacetals A series of <sup><i>t</i></sup>Bu-substituted <i>Z</i>-oligodiacetylenes (<i>Z</i>-ODAs) are synthesized from the reactions of allenyl/propargylic zinc reagents, obtained from the corresponding propargylic dithiolanes and BuLi, with dithiolane-substituted propargylic aldehydes followed by stereospecific elimination of β-thioalkoxy alcohols under Mitsunobu conditions. The stereochemical assignments are based on NOE experiments. The X-ray structure of the hexamer further supports the <i>Z</i> configuration for each of the double bonds in these ODAs. The photophysical properties of these <i>Z</i>-ODAs have been examined and are compared with known related <i>E</i>- and <i>Z</i>-ODAs with different substituents. thioalkoxy;BuLi;photophysical properties;allenyl;stereospecific elimination;hexamer;NOE experiments;aldehyde;bond;propargylic dithiolanes;Stereoselective Iterative Convergent Synthesis;Propargylic DithioacetalsA series;substituent;reagent;Z configuration;ODA;Mitsunobu conditions;stereochemical assignments 2015-09-04
    https://acs.figshare.com/articles/journal_contribution/Stereoselective_Iterative_Convergent_Synthesis_of_i_Z_i_Oligodiacetylenes_from_Propargylic_Dithioacetals/2134798
10.1021/acs.joc.5b01626.s001