Transition Metal-Mediated Intramolecular [2+2+2] Cycloisomerizations of Cyclic Triynes and Enediynes
- 11 February 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (6) , 2033-2041
- https://doi.org/10.1021/jo048056p
Abstract
Nitrogen-containing 15-membered triacetylenic macrocycles known as 1,6,11-tris(arylsulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-triynes (1) and enediynic macrocycles called 1,6,11-tris(arylsulfonyl)-1,6,11-triazacyclopentadeca-3-ene-8,13-diynes (4 and 5) were satisfactorily prepared. [2+2+2] cycloisomerization processes catalyzed by transition metals were tested in the above-mentioned macrocycles. Readily available and familiar cyclotrimerization precatalysts were examined for efficiency. Among them, the RhCl(CO)(PPh3)2 complex was found to catalyze the cycloisomerization reaction giving the desired cycloadducts in high yields.Keywords
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