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Palladium(II)‐Catalyzed Isomerization of ( Z )‐1,4‐Diacetoxy‐2‐Butene: Solvent Effects
Author(s) -
Zawisza Anna Maria,
Bouquillon Sandrine,
Muzart Jacques
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700246
Subject(s) - chemistry , isomerization , catalysis , solvent , reactivity (psychology) , palladium , solvent effects , medicinal chemistry , 2 butene , butene , organic chemistry , photochemistry , ethylene , medicine , alternative medicine , pathology
The isomerization of ( Z )‐1,4‐diacetoxy‐2‐butene ( 1 ) catalyzed by PdCl 2 (MeCN) 2 was studied in THF and DMF. The reaction occurs more rapidly in THF than in DMF, but in both solvents it did not proceed to complete consumption of the substrate and led to a mixture of 1 , ( E )‐1,4‐diacetoxy‐2‐butene ( 2 ), and 1,2‐diacetoxy‐3‐butene ( 3 ). The formation of 2 is more favored in DMF than in THF. The reactivity of 1 and the solvent effect differ strongly from those previously obtained with Pd(PPh 3 ) 4 as the catalyst. Interpretations are provided for the crucial role of the nature of both solvent and intermediates on the course of the isomerizations.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)