Open AccessAcid-Catalyzed Carbonylation of Lactone to Cyclic Anhydride on Tungsten Metal
Author(s) -
Lien Lee,
Ding-Jen Chen,
YingChih Lin,
YihHsing Lo,
Chien Hsing Lin,
GeneHsiang Lee,
Yu Wang
Publication year - 1997
Publication title -
organometallics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.231
H-Index - 172
eISSN - 1520-6041
pISSN - 0276-7333
DOI - 10.1021/om970431z
Subject(s) - chemistry , carbonylation , nucleophile , ligand (biochemistry) , catalysis , lactone , imine , yield (engineering) , medicinal chemistry , allylic rearrangement , ring (chemistry) , stereochemistry , polymer chemistry , organic chemistry , carbon monoxide , biochemistry , materials science , receptor , metallurgy
Facile carbonylation of the cis-vinyl complex Cp(CO)3W[CHCH(COMe)] (2, Cp = η5-C5H5) followed by cyclization affords the γ-lactone Further carbonylation of 4 induced by the presence of acid in CH3CN gives the cyclic anhydride The reaction of 4 with Me2NH causes ring opening to yield the zwitterionic complex Cp(CO)2W[η2-Me2NC(Me)CHCHCOOH] (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 and the reaction of NaBH4 with 9 generates the (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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