Synthesis and Properties of 2,3-Diethynyl-1,3-Butadienes
Date
2020
Authors
Sowden, Madison
Sherburn, Michael
Ward, James
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Abstract
The first general preparative access to compounds of
the 2,3-diethynyl-1,3-butadiene (DEBD) class is reported. The
synthesis involves a one-pot, twofold Sonogashira-type, Pd
0
-
catalyzed coupling of two terminal alkynes and a carbonate
derivative of a 2-butyne-1,4-diol. The synthesis is broad in
scope and members of this structural family are kinetically
stable enough to be handled using standard laboratory
techniques at ambient temperature. They decompose primarily
through heat-promoted cyclodimerizations, which are impeded
by alkyl substitution and accelerated by aryl or alkenyl
substitution. An iterative sequence of these unprecedented
Sonogashira-type couplings generates a new type of expanded
dendralene. A suitably substituted DEBD carrying two
terminal alkyne groups undergoes Glaser-Eglinton cyclooligomerization to produce a new class of expanded radialenes,
which are chiral due to restricted rotation about their 1,3-
butadiene units. The structural features giving rise to atropisomerism in these compounds are distinct from those reported
previously.
Description
Keywords
Citation
Collections
Source
Angewandte Chemie
Type
Journal article
Book Title
Entity type
Access Statement
License Rights
Restricted until
2037-12-31
Downloads
File
Description