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2.10.4.2.2 1,n-Bis-1,3-diynes

DOI: 10.1055/sos-SD-222-00346

Lee, D.; Reddy Sabbasani, V.Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (20162654.

The ring-closing alkyne metathesis of bis-1,3-diyne systems provides an unexpected outcome. Although the formation of three different cyclic products containing one, two, or three triple bonds is possible, the ring-closing alkyne metathesis of bis-1,3-diyne 574 upon treatment with tungsten–benzylidyne complex 554 bearing siloxide ligands selectively delivers 16-membered macrocyclic 1,3-diyne 575 in 90% yield along with hexa-2,4-diyne as byproduct (Scheme 126).[‌215‌] The generality of this selectivity is yet to be confirmed as this is the only example reported to date for ring-closing alkyne metathesis of bis-1,3-diynes (except for that shown in Section 2.10.4.3.4).

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