Show/Hide Menu
Hide/Show Apps
anonymousUser
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Videos
Videos
Thesis submission
Thesis submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Contact us
Contact us
Coupling of cyclobutenediones with Fischer carbene complexes: A one-step synthesis of cyclopentenediones and/or 5-alkylidenefuranones via net insertion of the carbene unit into a C-C bond
Date
1999-10-11
Author
Zora, Metin
LI, YH
HERNDON, JAMES W
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
20
views
0
downloads
Cite This
The reaction of Fischer carbene-chromium complexes with 3-cyclobutene-1,2-diones has been investigated. In most cases, the major product of the reaction is the C-C bond insertion product, a 2-alkoxy-4-cyclopentene-1,3-dione, accompanied by a minor amount of the partial deoxygenation product, a 4-cyclopentene-1,3-dione. In some cases, 5-alkylidenefuranones are also formed. A mechanism involving oxidative. addition of the coordinatively unsaturated Fischer carbene complex followed by acyl migration and reductive elimination was proposed to account for cyclopentenedione formation. Furanone formation was thought to arise via demetalation of the acyl migration product, followed by O-acylation. An electronic dependence was noted for cyclopentenedione/alkylidene-furanone ratio, which was evaluated using the Hammett equation.
Subject Keywords
Chromium
,
Rearrangement
,
Metabolites
URI
https://hdl.handle.net/11511/41948
Journal
ORGANOMETALLICS
DOI
https://doi.org/10.1021/om9905198
Collections
Department of Chemistry, Article
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
M. Zora, Y. LI, and J. W. HERNDON, “Coupling of cyclobutenediones with Fischer carbene complexes: A one-step synthesis of cyclopentenediones and/or 5-alkylidenefuranones via net insertion of the carbene unit into a C-C bond,”
ORGANOMETALLICS
, vol. 18, no. 21, pp. 4429–4436, 1999, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41948.