Synthesis 2012; 44(19): 3003-3005
DOI: 10.1055/s-0031-1290400
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A Large-Scale Synthesis of α-Olefins and α,ω-Dienes

George A. Kraus*
Department of Chemistry, Iowa State University, Ames, IA 50011, USA, Fax: +1(515)2940105   Email: gakraus@iastate.edu
,
Sean Riley
Department of Chemistry, Iowa State University, Ames, IA 50011, USA, Fax: +1(515)2940105   Email: gakraus@iastate.edu
› Author Affiliations
Further Information

Publication History

Received: 01 March 2012

Accepted after revision: 08 May 2012

Publication Date:
28 June 2012 (online)


Abstract

The decarbonylation of carboxylic acids or dicarboxylic acids in the presence of a palladium catalyst above 190 °C in the absence of a solvent constitutes a mild method for the large-scale synthesis of α-olefins and α,ω-dienes.

 
  • References

  • 1 Maercker A. Org. React. (N. Y.) 1965; 14: 270
  • 2 Carruthers W. Some Modern Methods of Organic Synthesis . Cambridge University Press; Cambridge: 1971: 81-90
  • 3 Goossen LJ, Rodriguez N. Chem. Commun. 2004; 724
  • 4 Le Notre J, Scott EL, Franssen MC. R, Sanders JP. M. Tetrahedron Lett. 2010; 51: 3712
  • 5 Maetani S, Fukuyama T, Suzuki N, Ishihara D, Ryu I. Organometallics 2011; 30: 1389
  • 6 Miller JA, Nelson JA, Byrne MP. J. Org. Chem. 1993; 58: 18
  • 7 Li Q, Li Y, Lin J, Zhu H, Liu F. Huaxue Yanjiu Yu Yingyong 1999; 11: 550 ; Chem. Abstr. 2000, 132, 194003
  • 8 Goossen LJ, Goossen K, Rodriguez N, Blanchot M, Linder C, Zimmermann B. Pure Appl. Chem. 2008; 80: 1725
  • 9 Gao Z.-L, Yin C.-x, Liu F.-C. Yunnan Daxue Xuebao, Ziran Kexueban 2001; 23: 201 ; Chem. Abstr. 2002, 136, 325035