THE PALLADIUM-CATALYZED INTRAMOLECULAR CYCLIZATION OF ALKADIENYL-SUBSTITUTED 1,3-DIKETONES

被引：30

作者：

GODDARD, R ^{[1
]}

HOPP, G ^{[1
]}

JOLLY, PW ^{[1
]}

KRUGER, C ^{[1
]}

MYNOTT, R ^{[1
]}

WIRTZ, C ^{[1
]}

机构：

[1] MAX PLANCK INST KOHLENFORSCH,D-45466 MULHEIM,GERMANY

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1995年 / 486卷 / 1-2期

关键词：

PALLADIUM CATALYSIS; INTRAMOLECULAR CYCLIZATION; 1,3-DIKETONES;

D O I：

10.1016/0022-328X(94)05017-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Hydroxydeca-3,7,9-triene-2-one (prepared by metallation of acetylacetone followed by treatment with 1-bromopenta-2,4-diene) undergoes intramolecular cyclization in the presence of a [Pd((Pr2PC2H4PPr2)-Pr-i-Pr-i)] catalyst to give a mixture of cyclohexanone and cycloheptenone derivatives. The cyclohexanone 2-(1-hydroxyethyliden)-3-vinylcyclohexanone isomerizes in the presence of palladium to give the palladium-alkene complex (eta(2)-2-acetyl-3-ethylcyclohex-2-enone)Pd((Pr2PC2H4PPr2)-Pr-i-Pr-i) whose crystal structure has been established by X-ray diffraction. A related cyclization reaction involving the disubstituted 1,3-diketone 9-hydroxy-1,3,7,12,14-pentaene-7-one leads to the formation of a mixture of spiro compounds (mainly 5,11-divinyl-spiro[5.5]undeca-1,7-dione) whose structures have been elucidated with the help of H-1- and C-13-NMR spectroscopies using D-2-NMR techniques.

引用

页码：163 / 170

页数：8

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