Isomerization of olefin carboxylic esters catalyzed by nickel and palladium compounds

✍ Scribed by Xiaotai Wang; L.Keith Woo

• Book ID: 104423587
• Publisher: Elsevier Science
• Year: 1998
• Tongue: English
• Weight: 160 KB
• Volume: 130
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/s1381-1169(97)00213-6

✦ Synopsis

Ž . w Ž . x The Group 10 complex trans-Pd C H CN Cl and acidic solutions of Ni P OEt effectively catalyze the stereoselec-6 5 2 2 3 4 w Ž . x tive isomerization of C5C double bonds in olefinic esters. With acidic solutions of Ni P OEt , only 4-pentenoate is 3 4

produced from 3-pentenoate at early times. However, in the presence of excess phosphite, 2-pentenoate is the only positional Ž . isomer produced 61% yield . In the absence of excess phosphite, a kinetically controlled process is proposed to explain the Ž . initial formation of 4-pentenoate. With the Pd catalyst, no 4-pentenoate is observed. For example, trans-Pd C H CN Cl 6 5 2 2 Ž . selectively produces 2-pentenoate from 3-pentenoate 58% . q 1998 Elsevier Science B.V.