Cyclic Diynes by Alkyne Metathesis

Abstract

The preparation of α,ω-diynes with methyl groups at the termini (11a-i) is described. The methylene groups between the alkyne units vary between n = 12 (a) and n = 4 (i). Ring closing metathesis with Mo(CO)₆/CF₃C₆H₄OH yielded the monocyclic alkyne 12a with 11a as starting material, whereas 11b-g yielded the cyclic diynes 13b-g. Detailed structural parameters were obtained for 13b and 13c by X-ray crystallography.

alkyne metathesis - cyclic diynes - cyclizations - macrocycles - molybdenum

References

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28a

Sheldrick G. M.; SHELXTL-PLUS V5.10; Bruker Analytical X-ray-Division: Madison, WI, 1997;

28b

Methylated α,ω-diynes react under alkyne metathesis conditions to cyclic diynes.