Chemistry: A European Journal 2011-04-18

Tandem insertion of halocarbenoids and lithium acetylides into zirconacycles: a novel rearrangement to zirconium alkenylidenates by β-addition to an alkynyl zirconocene.

Jozef Stec, Emma Thomas, Sally Dixon, Richard J Whitby

Index: Chemistry 17(17) , 4896-904, (2011)

Full Text: HTML

Abstract

Tandem insertion of 1,1-dihalo-1-lithio species (halocarbenoids) and lithium alkynides into zirconacyclopentenes and zirconcyclopentanes affords carbocyclic products in high yields via an unusual rearrangement that probably involves addition of an organolithium species to the β-position of a zirconium-alkyne complex to give an alkenylidene-zirconate species. A wide variety of cyclopentanoid organic structures are rapidly assembled in good yield using this multicomponent coupling. The main side reaction, which becomes exclusive in some cases, is β-hydride elimination of an intermediate cyclopentyl- or cyclopentenyl zirconocene.Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Related Compounds

  • Bis(cyclopentadien...

Related Articles:

Unusual temperature effects in propene polymerization using stereorigid zirconocene catalysts.

2003-02-15

[ChemPhysChem 6(9) , 1929-33, (2005)]

Enantioselective route from carbohydrates to cyclooctane polyols.

2005-02-03

[Org. Lett. 7(3) , 511-3, (2005)]

Functionalised cyclopentadienyl zirconium compounds as potential anticancer drugs.

2008-10-21

[Dalton Trans. (39) , 5293-5, (2008)]

Formal total synthesis of (+/-)-estrone and zirconocene-promoted cyclization of 2-fluoro-1,7-octadienes and ru-catalyzed ring closing metathesis.

2008-08-15

[J. Org. Chem. 73(16) , 6202-6, (2008)]

In pursuit of pestalotiopsin a via zirconocene-mediated ring contraction.

2006-05-25

[Org. Lett. 8(11) , 2429-31, (2006)]

More Articles...