Eglinton reaction

Oxidative coupling of terminal alkynes mediated by stoichiometric (often excess) Cu(OAc 2. a variant of the Glaser coupling reaction (page 160). 

---

The Glaser reaction is an oxidative coupling of terminal alkynes 1 to yield a symmetrical Z -acetylene 2 the coupling step is catalyzed by a copper salt. Closely related is the Eglinton reaction, which differs from the Glaser reaction mainly by the use of stoichiometric amounts of copper salt as oxidizing agent. 

The Eglinton Reaction is an oxidative coupling of terminal alkynes, and allows the synthesis of symmetric or cyclic bisacetylenes via reaction of the terminal alkyne with a stoichiometric amount of a copper(II) salt in pyridine. 

The Glaser Coupling (or Hay Coupling) is a synthesis of symmetric or cyclic bisacetylenes via a coupling reaction of terminal alkynes. Mechanistically, the reaction is similar to the Eglinton Reaction the difference being the use of catalytic copper(I), which is reoxidized in the catalytic cycle by oxygen in the reaction medium. 

Another reaction in which the Cu(I)/Cu(II) couple plays a central role is the Eglinton reaction. 

Eglinton reaction The symmetrical coupling of terminal alkynes by heating with stoichiometric amounts of cupric salts in pyridine, or a similar base. 

In the Eglinton reaction, terminal alkynes, R-C=C-H, are coupled in the presence of a Cu(II) salt and a base such as pyridine to form dialkynes. 

Glaser Coupling Eglinton Reaction Cadiot-Chodkiewicz Coupling... 

This coupling may also be effected by cupric salts in pyridine and is often referred to as the Eglinton reaction. It is particularly applicable to cyclizations G. Eglinton, A. R. Galbraith, Chem. Ind. (London) 1956,13>1 N. Hebert et al, J. Org. Chem. 57, 1777 (1992). 

---