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Transition metal-mediated intramolecular [2+2+2] cycloisomerizations of cyclic triynes and enediynes.
J Org Chem. 2005 Mar 18; 70(6):2033-41.JO

Abstract

[reaction: see text] 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)(PPh(3))(2) complex was found to catalyze the cycloisomerization reaction giving the desired cycloadducts in high yields.

Authors+Show Affiliations

Department of Chemistry, Universitat de Girona, Campus de Montilivi, s/n. E-17071-Girona, Spain. anna.roglans@udg.esNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15760184

Citation

Torrent, Anna, et al. "Transition Metal-mediated Intramolecular [2+2+2] Cycloisomerizations of Cyclic Triynes and Enediynes." The Journal of Organic Chemistry, vol. 70, no. 6, 2005, pp. 2033-41.
Torrent A, González I, Pla-Quintana A, et al. Transition metal-mediated intramolecular [2+2+2] cycloisomerizations of cyclic triynes and enediynes. J Org Chem. 2005;70(6):2033-41.
Torrent, A., González, I., Pla-Quintana, A., Roglans, A., Moreno-Mañas, M., Parella, T., & Benet-Buchholz, J. (2005). Transition metal-mediated intramolecular [2+2+2] cycloisomerizations of cyclic triynes and enediynes. The Journal of Organic Chemistry, 70(6), 2033-41.
Torrent A, et al. Transition Metal-mediated Intramolecular [2+2+2] Cycloisomerizations of Cyclic Triynes and Enediynes. J Org Chem. 2005 Mar 18;70(6):2033-41. PubMed PMID: 15760184.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Transition metal-mediated intramolecular [2+2+2] cycloisomerizations of cyclic triynes and enediynes. AU - Torrent,Anna, AU - González,Iván, AU - Pla-Quintana,Anna, AU - Roglans,Anna, AU - Moreno-Mañas,Marcial, AU - Parella,Teodor, AU - Benet-Buchholz,Jordi, PY - 2005/3/12/pubmed PY - 2005/6/9/medline PY - 2005/3/12/entrez SP - 2033 EP - 41 JF - The Journal of organic chemistry JO - J Org Chem VL - 70 IS - 6 N2 - [reaction: see text] 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)(PPh(3))(2) complex was found to catalyze the cycloisomerization reaction giving the desired cycloadducts in high yields. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15760184/Transition_metal_mediated_intramolecular_[2+2+2]_cycloisomerizations_of_cyclic_triynes_and_enediynes_ L2 - https://doi.org/10.1021/jo048056p DB - PRIME DP - Unbound Medicine ER -