Premium
Palladium(0)‐Catalyzed Isomerization of ( Z )‐1,4‐Diacetoxy‐2‐butene − Dependence of η 1 ‐ or η 3 ‐Allylpalladium as a Key Intermediate on the Solvent Polarity
Author(s) -
Bouquillon Sandrine,
Muzart Jacques
Publication year - 2001
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 - 10.1002/1099-0690(200109)2001:17<3301::aid-ejoc3301>3.0.co;2-s
Subject(s) - chemistry , isomerization , cationic polymerization , 2 butene , palladium , catalysis , solvent , butene , solvent polarity , 1 butene , medicinal chemistry , organic chemistry , photochemistry , ethylene
In the presence of Pd(PPh 3 ) 4 , ( Z )‐1,4‐diacetoxy‐2‐butene is selectively isomerized to ( E )‐1,4‐diacetoxy‐2‐butene in THF while both ( E )‐1,4‐diacetoxy‐2‐butene and 1,2‐diacetoxy‐3‐butene are obtained in DMF. Evidence to support the involvement of an η 1 ‐allylpalladium in the former solvent and of a cationic η 3 ‐allylpalladium in the latter as the keys intermediates is presented.