Low pressure carbonylation of heterocycles
Abstract
Heterocycles, e.g., epoxides, are carbonylated at low pressure with high percentage conversion to cyclic, ring expanded products using the catalyst ##STR00001## where L is tetrahydrofuran (THF).
- Inventors:
-
- Lansing, NY
- Mt. Pleasant, MI
- Sylvania, OH
- Issue Date:
- Research Org.:
- Cornell Univ., Ithaca, NY (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1012917
- Patent Number(s):
- 7875734
- Application Number:
- 12/486,158
- Assignee:
- Cornell Research Foundation, Inc. (Ithaca, NY)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- FG02-05ER15687
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Coates, Geoffrey W, Kramer, John W, and Schmidt, Joseph A. R. Low pressure carbonylation of heterocycles. United States: N. p., 2011.
Web.
Coates, Geoffrey W, Kramer, John W, & Schmidt, Joseph A. R. Low pressure carbonylation of heterocycles. United States.
Coates, Geoffrey W, Kramer, John W, and Schmidt, Joseph A. R. Tue .
"Low pressure carbonylation of heterocycles". United States. https://www.osti.gov/servlets/purl/1012917.
@article{osti_1012917,
title = {Low pressure carbonylation of heterocycles},
author = {Coates, Geoffrey W and Kramer, John W and Schmidt, Joseph A. R.},
abstractNote = {Heterocycles, e.g., epoxides, are carbonylated at low pressure with high percentage conversion to cyclic, ring expanded products using the catalyst ##STR00001## where L is tetrahydrofuran (THF).},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2011},
month = {1}
}
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Works referenced in this record:
Fluorine containing?-lactones: Part 2. ?-Trifluoromethyl-?-methyl-?-propiolactone
journal, May 1961
- Knunyants, I. L.; Cheburkov, Yu. A.
- Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 10, Issue 5
Predicting the R/S absolute configuration in asymmetric bifunctional catalysis (ABC)
journal, July 2007
- Lin, Yun-Ming; Li, Zhongtao; Boucau, Julie
- Tetrahedron Letters, Vol. 48, Issue 30
Free radical catalysed additions to the double bond of diketene: a synthesis of novel oxetan-2-ones
journal, January 1986
- Dingwall, John G.; Tuck, Brian
- Journal of the Chemical Society, Perkin Transactions 1
Inversion of Configuration of (S)-β-Hydroxy-γ-butyrolactone with Total Retention of the Enantiomeric Purity
journal, November 1999
- De Angelis, Francesco; De Fusco, Enrico; Desiderio, Paola
- European Journal of Organic Chemistry, Vol. 1999, Issue 11, p. 2705-2707
A de Novo Enantioselective Total Synthesis of (−)-Laulimalide
journal, November 2002
- Nelson, Scott G.; Cheung, Wing S.; Kassick, Andrew J.
- Journal of the American Chemical Society, Vol. 124, Issue 46
A Readily Synthesized and Highly Active Epoxide Carbonylation Catalyst Based on a Chromium Porphyrin Framework: Expanding the Range of Available β-Lactones
journal, February 2004
- Schmidt, Joseph A. R.; Mahadevan, Viswanath; Getzler, Yutan D. Y. L.
- Organic Letters, Vol. 6, Issue 3, p. 373-376
Synthesis of β-Lactones by the Regioselective, Cobalt and Lewis Acid Catalyzed Carbonylation of Simple and Functionalized Epoxides
journal, August 2001
- Lee, Jong Tae; Thomas, P. J.; Alper, Howard
- The Journal of Organic Chemistry, Vol. 66, Issue 16
Poly(β-malic acid) derivatives with non-charged hydrophilic lateral groups: synthesis and characterization
journal, December 1999
- Barbaud, Christel; Cammas-Marion, Sandrine; Guérin, Philippe
- Polymer Bulletin, Vol. 43, Issue 4-5
Addressing the competition between intramolecular acyl and beta ring cleavage in β-lactones
journal, March 1997
- White, Dominique; Zemribo, Ronald; Mead, Keith T.
- Tetrahedron Letters, Vol. 38, Issue 13
Synthesis and Characterization of New Malolactonate Polymers and Copolymers for Biomedical Applications
journal, February 2002
- Bizzarri, Ranieri; Chiellini, Federica; Solaro, Roberto
- Macromolecules, Vol. 35, Issue 4
Isomerization polymerization of β-propiolactones carrying side-chain ester groups
journal, June 1983
- Araki, Takeo; Hayase, Shuzi; Nakamura, Akira
- Journal of Polymer Science: Polymer Chemistry Edition, Vol. 21, Issue 6
Practical β-Lactone Synthesis: Epoxide Carbonylation at 1 atm
journal, August 2006
- Kramer, John W.; Lobkovsky, Emil B.; Coates, Geoffrey W.
- Organic Letters, Vol. 8, Issue 17
Chromium(III) Octaethylporphyrinato Tetracarbonylcobaltate: A Highly Active, Selective, and Versatile Catalyst for Epoxide Carbonylation
journal, August 2005
- Schmidt, Joseph A. R.; Lobkovsky, Emil B.; Coates, Geoffrey W.
- Journal of the American Chemical Society, Vol. 127, Issue 32
Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensations. A Strategy for Enantioselective Catalyzed Cross Aldol Reactions
journal, October 1999
- Nelson, Scott G.; Peelen, Timothy J.; Wan, Zhonghui
- Journal of the American Chemical Society, Vol. 121, Issue 41
Catalytic Carbonylation of β-Lactones to Succinic Anhydrides
journal, June 2004
- Getzler, Yutan D. Y. L.; Kundnani, Vinod; Lobkovsky, Emil B.
- Journal of the American Chemical Society, Vol. 126, Issue 22, p. 6842-6843
Liquid-crystalline properties of chiral malolactonate monomers and their comb-shaped polymers
journal, October 1992
- Fujishiro, Koichi; Lenz, Robert W.
- Liquid Crystals, Vol. 12, Issue 4
A stannous chloride-induced deacetalisation–cyclisation process to prepare the ABC ring system of 'upenamide
journal, May 2004
- Reid, Mark; Taylor, Richard J. K.
- Tetrahedron Letters, Vol. 45, Issue 21
Use of In Situ Generated Ketene in the Wynberg β-Lactone Synthesis: New Transformations of the Dichlorinated β-Lactone Products
journal, October 2000
- Tennyson, Reginald; Romo, Daniel
- The Journal of Organic Chemistry, Vol. 65, Issue 21
Selective synthesis of structurally isomeric poly-β-ester and poly-δ-ester from β-(2-acetoxy-ethyl)-β-propiolactone with Al and Zn catalysts
journal, December 1982
- Araki, Takeo; Hayase, Shuzi; Nakamura, Akira
- Journal of Polymer Science: Polymer Chemistry Edition, Vol. 20, Issue 12
Synthesis of stereoregular poly(alkyl malolactonates)
journal, December 1986
- Arnold, Steven C.; Lenz, Robert W.
- Makromolekulare Chemie. Macromolecular Symposia, Vol. 6, Issue 1
Poly(β -malic acid) derivatives with unsaturated lateral groups: epoxidation as model reaction of the double bonds reactivity
journal, August 1996
- Leboucher-Durand, Marie-Agnès; Langlois, Valérie; Guérin, Philippe
- Reactive and Functional Polymers, Vol. 31, Issue 1
Polymers of malic acid conjugated with the 1-adamantyl moiety as lipophilic pendant group
journal, June 1997
- Moine, Laurence; Cammas, Sandrine; Amiel, Catherine
- Polymer, Vol. 38, Issue 12
Influence of structural parameters on the ring-opening polymerization of new alkyl malolactonate monomers and on the biocompatibility of polymers therefrom
journal, July 2002
- Bizzarri, Ranieri; Chiellini, Federica; Ober, Chris K.
- Macromolecular Chemistry and Physics, Vol. 203, Issue 10-11, p. 1684-1693
Divergent reaction pathways in amine additions to β-lactone electrophiles. An application to β-peptide synthesis
journal, August 2002
- Nelson, Scott G.; Spencer, Keith L.; Cheung, Wing S.
- Tetrahedron, Vol. 58, Issue 35
Preparation and use of novel (S)-β-chlorodifluoromethyl-β-propiolactone as a chiral fluorinated building block
journal, May 1998
- Ito, Takatoshi; Shimizu, Makoto; Fujisawa, Tamotsu
- Tetrahedron, Vol. 54, Issue 21
cis, cis-und trans, trans-1-Methyl-4-hydroxy-3, 5-bis (athoxycarbonylmethyl) piperidin.
journal, January 1959
- Tsuda, Kyosuke; Sakai, Kiyoshi
- CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 7, Issue 2
Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene−Aldehyde Cycloadditions
journal, May 2004
- Zhu, Cheng; Shen, Xiaoqiang; Nelson, Scott G.
- Journal of the American Chemical Society, Vol. 126, Issue 17
Catalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation Reaction
book, October 2005
- Nelson, Scott G.; Mills, Paul M.
- Organic Syntheses
4-Carboxy-2-oxetanone as a new chiral precursor in the preparation of functionalized racemic or optically active poly(malic acid) derivatives
journal, January 1996
- Leboucher-Durand, Marie-Agn�s; Langlois, Val�rie; Guerin, Philippe
- Polymer Bulletin, Vol. 36, Issue 1
Selective synthesis of structurally isomeric poly(β-ester) and poly(δ-ester) from β-(2-acetoxyethyl)-β-propiolactone. A new difference between (EtAlO)n and Et(ZnO)2 ZnEt catalyses
journal, October 1978
- Araki, Takeo; Hayase, Shuji; Iida, Makoto
- Journal of Polymer Science: Polymer Letters Edition, Vol. 16, Issue 10