Stereoselective Iterative Convergent Synthesis of Z-Oligodiacetylenes from Propargylic Dithioacetals
Journal
Journal of Organic Chemistry
Journal Volume
80
Journal Issue
17
Pages
8772-8781
Date Issued
2015
Author(s)
Abstract
A series of (t)Bu-substituted Z-oligodiacetylenes (Z-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 Z configuration for each of the double bonds in these ODAs. The photophysical properties of these Z-ODAs have been examined and are compared with known related E- and Z-ODAs with different substituents.
Type
journal article