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Org Lett

Title:		"Double-Bond Isomerization: Highly Reactive Nickel Catalyst Applied in the Synthesis of the Pheromone (9Z,12Z)-Tetradeca-9,12-dienyl Acetate"
Author(s):		Weber F; Schmidt A; Rose P; Fischer M; Burghaus O; Hilt G;
Address:		"Fachbereich Chemie, Philipps-Universitat Marburg, Hans-Meerwein-Strasse 4, D-35043 Marburg, Germany"
Journal Title:		Org Lett
Year:		2015
Volume:		20150529
Issue:		12
Page Number:		2952 - 2955
DOI:		10.1021/acs.orglett.5b01230
ISSN/ISBN:		1523-7052 (Electronic) 1523-7052 (Linking)
Abstract:		"A highly reactive nickel catalyst comprising NiCl2(dppp) or NiCl2(dppe) with zinc powder, ZnI2 and Ph2PH, was applied in the isomerization of terminal alkenes to Z-2-alkenes. The double-bond geometry of the 2-alkene can be controlled via the reaction temperature to yield the 2-Z-alkenes in excellent yields and high Z-selectivities. The formation of other constitutional isomers, such as 3-alkenes, is suppressed on the basis of the proposed mechanism via a 1,2-hydride shift from the metal to the Ph2P ligand. The nickel-catalyzed isomerization reaction was then applied in the synthesis of (9Z,12Z)-tetradeca-9,12-dienyl acetate, a pheromone with a 2Z,5Z-diene subunit"
Keywords:
Notes:		"PubMed-not-MEDLINEWeber, Felicia Schmidt, Anastasia Rose, Philipp Fischer, Michel Burghaus, Olaf Hilt, Gerhard eng 2015/05/30 Org Lett. 2015 Jun 19; 17(12):2952-5. doi: 10.1021/acs.orglett.5b01230. Epub 2015 May 29"