Acid-catalyzed carbonylation of lactone to cyclic anhydride on tungsten metal

被引：13

作者：

Lee, L ^{[1
]}

Chen, DJ ^{[1
]}

Lin, YC ^{[1
]}

Lo, YH ^{[1
]}

Lin, CH ^{[1
]}

Lee, GH ^{[1
]}

Wang, Y ^{[1
]}

机构：

[1] NATL TAIWAN UNIV, DEPT CHEM, TAIPEI 10764, TAIWAN

来源：

ORGANOMETALLICS | 1997年 / 16卷 / 21期

关键词：

D O I：

10.1021/om970431z

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Facile carbonylation of the cis-vinyl complex Cp(CO)(3)W[CH=CH(COMe)] (2, Cp = eta(5)-C5H5) followed by cyclization affords the gamma-lactone complex Cp(CO)(2)W[eta(3)-CHCHC(Me)OC(O)] (4). Further carbonylation of 4 induced by the presence of acid in CH3CN gives the cyclic anhydride complex Cp(CO)(CH3CN)W[eta(3)-CHCHC(Me)C(O)OC(O)] (9). The reaction of 4 with Me2NH causes ring opening to yield the zwitterionic complex Cp(CO)(2)W[eta(2)-Me2N=C(Me)CH=CHCOOH] (6). The cyclic anhydride ligand of 9 remains unchanged when 9 is treated with nucleophiles. For example, the reaction of Me2NH with 9 affords the imine-coordinated complex Cp(CO)(Me2NC(Me)=NH)W[eta(3)-CHCHC(Me)C(O)OC(O)] (14), and the reaction of NaBH4 with 9 generates the amine-coordinated complex Cp(CO)(MeCH2NH2)W[eta(3)-CHCHC(Me)C(O)OC(O)] (15). The structures of 4, 6, 9, and 14 have also been determined by X-ray diffraction analysis. The allylic ligand in 9 is in an endo conformation.

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页码：4636 / 4644

页数：9

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