Regioselective Homo- and Codimerization of 1-Alkynes Leading to 2,4-Disubstituted 1-Buten-3-ynes by Catalysis of a (η5-C5Me5)2TiCl2/RMgX System
- 1 February 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 57 (2), 480-487
- https://doi.org/10.1246/bcsj.57.480
Abstract
A series of 1-alkynes (RC≡CH where R=Et, n-Pr, n-Bu, n-C6H13, cyclohexyl, Ph, Me3Si, Me3SiCH2, and Me3SiOCH2) was found to dimerize regioselectively (>99%) to 2,4-disubstituted 1-buten-3-ynes in 92–99% yields by catalysis of (η5-C5Me5)2TiCl2/i-PrMgBr at 30 °C in 1–3 h. The catalyst system is also effective for the regioselective codimerization of various 1-alkynes with 1-ethynylcyclohexene or ethynylbenzene.Keywords
This publication has 24 references indexed in Scilit:
- Transition-metal-catalyzed acetylene cyclizations in organic synthesisAccounts of Chemical Research, 1977
- Structure and chemistry of bis(cyclopentadienyl)-MLn complexesJournal of the American Chemical Society, 1976
- Facile synthesis of tert-butylacetyleneThe Journal of Organic Chemistry, 1974
- Rearrangement of .alpha.-ethynyl alcohols to unsaturated carbonyl compounds (The Rupe Reaction)The Journal of Organic Chemistry, 1973
- The Homogeneous Hydrogenation of Acetylenes by DicyclopentadienyltitaniumdicarbonylBulletin of the Chemical Society of Japan, 1966
- The Cyclic Trimerization of Acetylenes Over a Ziegler CatalystJournal of the American Chemical Society, 1961
- Catalytic Dimerization of Monoalkyl AcetylenesBulletin of the Chemical Society of Japan, 1961
- The chemistry of acetylenic ethers XVI. Acetylenic thioethersRecueil des Travaux Chimiques des Pays-Bas, 1956
- Bis-cyclopentadienyl Compounds of Ti, Zr, V, Nb and TaJournal of the American Chemical Society, 1954
- Reduction of Some Grignard Reagent-Carbon Dioxide Adducts to Primary Alcohols by Lithium Aluminum HydrideJournal of the American Chemical Society, 1954