Eglinton conditions

Oxidative coupling55 of the acetylenic alcohol 146 under Eglinton conditions followed by acidic treatment of the product gave the aldehydes 147 (37%) and 148 (8%). Wittig reaction of aldehyde 147 and the bisphosphonium salt 120 with 1,5-diazabicyclo[4.3.0]non-5-ene as base gave the [21]annulenone 149. This on reduction with lithium aluminium hydride-aluminium chloride gave the homoannulene... 

The use of Cu(OAc)2 under the Eglinton conditions also effects homocoupling of both alkynyltrimethylsilanes, 26— 27, and dialkynyl-... 

All three coupling procedures are suitable to give high yields under mild reaction conditions. Many functional groups do not interfere. For the application in organic synthesis the Eglinton variant may be more convenient than the Glaser method a drawback however is the need for stoichiometric amounts of copper salt. 

Sauer, P. E., Eglinton, T. I., Hayes, J. M., Schimmelmann, A. and Sessions, A. L. (2001) Compound specific D/H ratios of lipid biomarkers from sediments as a proxy for environmental and climatic conditions. Geochimica et Cosmochimica Acta 65, 213 222. 

In 1954, Eglinton et al. [235] reported the reaction of ethyl 2,3-butadienoate with NaOEt in EtOH. It was observed that the product is ethyl 2-ethoxy-2-butenoate, showing that the C=C bond migrated from the /3,/-position to the a,/3-position under the basic conditions [235],... 

Didyk, B.M., Simoneit, B.R.T., Brassell, S.C., and Eglinton, G. (1978) Organic geochemical indicators of paleoenvironmental conditions of sedimentation. Nature 272, 216-222. 

Four donor acceptor [2]catenanes possessing cyclobis(paraquat-p-phenylene), as the 7i-electron acceptor, and 1,5-dioxynaphthalene-containing macrocyclic polyethers, as the 7i-electron donor moieties, have been constructed employing Cu+-catalyzed Huisgen 1,3-dipolar cycloaddition and Cu+2-mediated Eglinton coupling condition in the final step <07JA8236>. Desymmetrized [2]catenanes were synthesized by means of a template synthesis of pseudorotaxanes between 7i-rich crown ethers and a 7i-deficient pyromellitic subunit,... 

Misumi and his coworkers have prepared 1,3-cycIotetradecadiyne (14S) and 1,3-cyclotridecadiyne (146) by Eglinton s oxidative coupling under high dilution conditions of the corresponding a,co-diynes - . 1,3-Tridecadiyne (146), the smallest... 

Weaver P. P. E., Chapman M. R., Eglinton G., Zhao M., Rutledge D., and Read G. (1999) Combined coccoUth, foraminiferal, and biomarker reconstmction of paleoceano-graphy conditions over the past 120 kyr in the northern North Atlantic (59° N, 23° W). Paleoceanography 14, 336-349. 

Didyk, B. M., B. R. T. Simoneit, S. C. Brassel, and G. Eglinton (1978). Organic geochemical indicators of paleo-environmental conditions of sedimention. Nature 272, 216-222. 

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