Application of the Nicholas reaction to the synthesis of dicobalt hexacarbonyl complexed diyne ethers

Amin, Jahangir, Motevalli, Majid and Richards, Christopher J. ORCID: https://orcid.org/0000-0001-7899-4082 (2015) Application of the Nicholas reaction to the synthesis of dicobalt hexacarbonyl complexed diyne ethers. Journal of Organometallic Chemistry, 776. pp. 43-50. ISSN 0022-328X

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Abstract

Addition of propargylic or homopropargylic ynols to dicobalt hexacarbonyl propargylium cations gave the expected ether products of the Nicholas reaction, with the exception of 4-phenyl-3-butyn-1-ol which gave a dihydrofuran due to propargylium cation promoted 5-endo ring-closure. Use of chiral dicobalt hexacarbonyl complexed propargylic ynols as both propargylium cation precursor and nucleophile gave racemic doubly complexed disymmetric diyne ethers, each as a single diastereoisomer. Addition of dicobalt hexacarbonyl complexed 1-phenyl-1-butyne-3-ene to the propargylium cation derived from dicobalt hexacarbonyl complexed 1-phenyl-1-butyn-3-ol, followed by the addition of a nucleophile (NuH), gave double complexed 1,7-diphenyl-3-Nu-5-methylhepta-1,6-diynes (d.r. > 10:1).

Item Type: Article
Uncontrolled Keywords: alkynes,cobalt,ethers,cations,diastereoselective
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Pure Connector
Date Deposited: 02 Feb 2015 15:52
Last Modified: 30 Sep 2022 00:51
URI: https://ueaeprints.uea.ac.uk/id/eprint/52069
DOI: 10.1016/j.jorganchem.2014.10.030

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