
Overview
Background
Educated at the University of Copenhagen, Denmark, and the Australian National University, Canberra. Career at the Université de Lausanne, Switzerland, and the Universität Marburg, Germany. Professor and Chair of Organic Chemistry and Head of the Organic Chemistry Section, The University of Queensland from 1985. Emeritus professor from 2008. Chair of the National Committee for Chemistry of the Australian Academy of Science 2009-2014. Editor-in-Chief, Australian Journal of Chemistry 2008-15. Editor, Journal of Analytical and Applied Pyrolysis (Elsevier, IF 3.65) 2016-. Visiting Professor Université de Pau, France, 2011-19; Visiting Professor University of Kuwait 2014-18; Visiting Professor / Special Appointed Professor Hiroshima University 2014-18. Fellow of the Australian Academy of Science. Centenary Medal of the Australian Commonwealth 2003 for research in organic and physical chemistry. David Craig Medal of the Academy of Science 2014 for research in chemistry. JSPS Fellowship (Japan) 2014. Honorary doctorate, University of Pau, France, 2014. A.J. Birch Medal of the Royal Australian Chemical Institute (RACI) for ecellence in research in organic chemistry, 2014. Leighton Medal of the RACI 2018.
Research on Unusual Molecules and Reactive Intermediates: Synthesis and Reaction Mechanism. Heterocyclic chemistry. Pyrolysis reactions. Photochemistry
Research in the Wentrup group is concerned with the discovery of novel types of molecules with new and unusual bonding patterns. Such molecules are mostly highly reactive, and special methods are required both for their generation and for their detection. The group has developed these methods over many years and acquired world-class equipment for these purposes, including flash vacuum thermolysis apparatus, cryostats for matrix isolation of reaction products at cryogenic temperatures (down to 7 K), matrix and solution photochemistry equipment, infrared, UV and mass spectrometers, as well as modern computational facilities.
This research has resulted in the synthesis and characterization of many novel compounds, including extended cumulenes of the types RN=C=C=C=X, which themselves are used in the synthesis of many novel types of molecules, some of them of potential pharmaceutical interest (quinolone antibiotics; diazepines).
The research group has a world reputation in the field of carbene and nitrene chemistry, involving reactive intermediates with sextet carbon or nitrogen. These species are also very useful in synthesis, for example in the preparation of diazepines and diazepinones, a family of pharmaceutically interesting compounds. Numerous mechanistic studies and synthetic applications of ketenes have been carried out in our group.
Active collaborations are ongoing with scientists in Australia (UQ and CSIRO), China (Suzhou), France (Pau), Germany (Oldenburg), Japan (Hiroshima), Spain (Donostia - San Sebastian), and Portugal (Coimbra).
Availability
- Emeritus Professor Curt Wentrup is:
- Not available for supervision
- Media expert
Fields of research
Qualifications
- Doctor of Philosophy, Australian National University
- Doctor of Philosophy of Science (Advanced), University of Copenhagen
- Doctoral Diploma, Institution to be confirmed
- Australian Academy of Science, Australian Academy of Science
- Royal Australian Chemical Institute, Royal Australian Chemical Institute
Research interests
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Organic, physical, and historical chemistry
Reactive intermediates, pyrolysis, photochemistry, reaction mechanism. History of science.
Research impacts
This research leads to the development of new pharmaceuticals, e.g. new antibiotics (quinolones and naphthyridones) and new leads towards a treatment for scizophrenia (diazepine molecules).
Chemical industry has used our pyrolysis techniques in specialized manufacturing processes.
Our analytical/spectroscopic work has led to cooperation with chemical and energy firms and agencies involved in forensic science, and our research has generated collaborations with many scientists at universities in Australia, Austria, Belgium, China, Denmark, France, Germany, Hungary, Japan, Portugal, Singapore, Switzerland, and USA.
Works
Search Professor Curt Wentrup’s works on UQ eSpace
2006
Journal Article
Nitrenes, diradicals, and ylides. Ring expansion and ring opening in 2-quinazolylnitrenes
Kvaskoff, D., Bednarek, P., George, L., Waich, K. and Wentrup, C. (2006). Nitrenes, diradicals, and ylides. Ring expansion and ring opening in 2-quinazolylnitrenes. Journal of Organic Chemistry, 71 (11), 4049-4058. doi: 10.1021/jo052541i
2005
Journal Article
Ketene-ketenimine rearrangements in the gas phase and in polar media. 1,3-migration intermediates and sequential transition states
Finnerty, Justin J. and Wentrup, Curt (2005). Ketene-ketenimine rearrangements in the gas phase and in polar media. 1,3-migration intermediates and sequential transition states. Journal of Organic Chemistry, 70 (24), 9735-9739. doi: 10.1021/jo051389h
2005
Journal Article
Erratum: Different behavior of nitrenes and carbenes on photolysis and thermolysis: Formation of azirine, ylidic cumulene, and cyclic ketenimine and the rearrangement of 6-phenanthridylcarbene to 9-phenanthrylnitrene (Journal of Organic Chemistry (2005) 7
Kvaskoff, David, Bednarek, Pawel, George, Lisa, Pankajakshan, Sreekumar and Wentrup, Curt (2005). Erratum: Different behavior of nitrenes and carbenes on photolysis and thermolysis: Formation of azirine, ylidic cumulene, and cyclic ketenimine and the rearrangement of 6-phenanthridylcarbene to 9-phenanthrylnitrene (Journal of Organic Chemistry (2005) 7. Journal of Organic Chemistry, 70 (23), 9666-9666. doi: 10.1021/jo052043
2005
Journal Article
N-(3,5-dichloro-2-pyridyl) formamide
Reisinger, Ales, Wentrup, Curt, Byriel, Karl A. and Kennard, Colin H. L. (2005). N-(3,5-dichloro-2-pyridyl) formamide. Acta Crystallographica Section E-Structure Reports Online, 61 (7), o2053-o2054. doi: 10.1107/S1600536805017605
2005
Journal Article
N,N-Dialkyl-N'-(2-pyridyl)formamidines and N-(3,5-dichloro-2-pyridyl) formamide. Reactions of azides, tetrazoles and nitrenes with nucleophiles. Part 1
Reisinger, Ales and Wentrup, Curt (2005). N,N-Dialkyl-N'-(2-pyridyl)formamidines and N-(3,5-dichloro-2-pyridyl) formamide. Reactions of azides, tetrazoles and nitrenes with nucleophiles. Part 1. Arkivoc, 2005 (xiv), 131-134. doi: 10.3998/ark.5550190.0006.e15
2005
Journal Article
A cyclopropabenzenylidenethenone (Propadienone) via a new route to alkylidenecycloproparenes
Halton, B., Dixon, G., Jones, C. M., Parkin, C. T., Naduvile Veedu, R., Bornemann, H. and Wentrup, C. (2005). A cyclopropabenzenylidenethenone (Propadienone) via a new route to alkylidenecycloproparenes. Organic Letters, 7 (5), 949-952. doi: 10.1021/ol050095f
2005
Journal Article
Energy profiles for ketene cyclizations. interconversion of 1,3-oxazin-6-ones, mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products
Bornemann, Holger and Wentrup, Curt (2005). Energy profiles for ketene cyclizations. interconversion of 1,3-oxazin-6-ones, mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products. Journal of Organic Chemistry, 70 (15), 5862-5868. doi: 10.1021/jo050429e
2005
Journal Article
Different behavior of nitrenes and carbenes on photolysis and thermolysis: Formation of azirine, ylidic cumulene, and cyclic ketenimine and the rearrangement of 6-phenanthridylcarbene to 9-phenanthrylnitrene
Kvaskoff, David, Bednarek, Pawel, George, Lisa, Pankajakshan, Sreekumar and Wentrup, Curt (2005). Different behavior of nitrenes and carbenes on photolysis and thermolysis: Formation of azirine, ylidic cumulene, and cyclic ketenimine and the rearrangement of 6-phenanthridylcarbene to 9-phenanthrylnitrene. Journal of Organic Chemistry, 70 (20), 7947-7955. doi: 10.1021/jo050898g
2005
Journal Article
Imidoylketene-alpha-oxoketenimine and alpha-oxoketene-alpha-oxoketene rearrangements. 1,3-Shifts of substituted phenyl groups
George, Lisa and Wentrup, Curt (2005). Imidoylketene-alpha-oxoketenimine and alpha-oxoketene-alpha-oxoketene rearrangements. 1,3-Shifts of substituted phenyl groups. Organic & Biomolecular Chemistry, 3 (16), 2998-3000. doi: 10.1039/B504260G
2005
Journal Article
The curtius rearrangement of acyl azides revisited - formation of cyanate (R-O-CN)
Wentrup, C. and Bornemann, H. (2005). The curtius rearrangement of acyl azides revisited - formation of cyanate (R-O-CN). European Journal of Organic Chemistry, 2005 (21), 4521-4524. doi: 10.1002/ejoc.200500545
2005
Journal Article
Mesoionic 1,3-oxazinium olates. Rearrangement to acylketenes and 3-azabicyclo[3.1.1]heptanetriones
Sheibani, H., Bernhardt, P. V. and Wentrup, C. (2005). Mesoionic 1,3-oxazinium olates. Rearrangement to acylketenes and 3-azabicyclo[3.1.1]heptanetriones. Journal of Organic Chemistry, 70 (15), 5859-5861. doi: 10.1021/jo050428m
2004
Journal Article
2,6,9-Trioxabicyclo[3.3.1]nona-3,7-dien-4-oyl and tetraoxaadamantan-9-oyl functionalized aromatic di- and triamines: Synthesis, stereochemistry and complexation
Heilmayer, W., Smounig, R., Gruber, K., Fabian, W. M. F., Reidlinger, C., Kappe, C. O., Wentrup, C. and Kollenz, G. (2004). 2,6,9-Trioxabicyclo[3.3.1]nona-3,7-dien-4-oyl and tetraoxaadamantan-9-oyl functionalized aromatic di- and triamines: Synthesis, stereochemistry and complexation. Tetrahedron, 60 (12), 2857-2867. doi: 10.1016/j.tet.2004.01.058
2004
Journal Article
2-benzyl-1-hydroxy-5,6,-dihydro-3H-naptho[2,1-b]pyran-3-one
Wentrup, Curt, Buchanan, Jeff, Byriel, Karl A. and Kennard, Colin H. L. (2004). 2-benzyl-1-hydroxy-5,6,-dihydro-3H-naptho[2,1-b]pyran-3-one. Acta Crystallographica Section E, 60 (3), o471-o472. doi: 10.1107/S1600536804003848
2004
Journal Article
Synthesis of 1,3-diazepines and ring contraction to cyanopyrroles
Reisinger, Ales, Bernhardt, Paul V. and Wentrup, Curt (2004). Synthesis of 1,3-diazepines and ring contraction to cyanopyrroles. Organic & Biomolecular Chemistry, 2 (2), 246-256. doi: 10.1039/b311247k
2004
Journal Article
Facile ketene-ketene and ketene-ketenimine rearrangements: A study of the 1,3-migration of alpha-substituents interconverting alpha-imidoylketenes and alpha-oxoketenimines, a pseudopericyclic reaction
Finnerty, J. J. and Wentrup, C. (2004). Facile ketene-ketene and ketene-ketenimine rearrangements: A study of the 1,3-migration of alpha-substituents interconverting alpha-imidoylketenes and alpha-oxoketenimines, a pseudopericyclic reaction. Journal of Organic Chemistry, 69 (6), 1909-1918. doi: 10.1021/jo035419x
2004
Journal Article
Ketene-acetylene [2+2] cycloadditions: cyclobutenone and/or oxete formation?
Koch, R. and Wentrup, C. (2004). Ketene-acetylene [2+2] cycloadditions: cyclobutenone and/or oxete formation?. Organic & Biomolecular Chemistry, 2 (2), 195-199. doi: 10.1039/b309549e
2004
Journal Article
Imidoylketene dimerization and rearrangement
George, L., Bernhardt, P. V., Netsch, K. P. and Wentrup, C. (2004). Imidoylketene dimerization and rearrangement. Organic & Biomolecular Chemistry, 2 (23), 3518-3523. doi: 10.1039/b412530d
2004
Journal Article
The rearrangements of naphthyinitrenes: UV/Vis and IR spectra of azirines, cyclic ketenimines, and cyclic nitrile ylides
Maltsev, A., Bally, T., Tsao, M. L., Platz, M. S., Kuhn, A., Vosswinkel, M. and Wentrup, C. (2004). The rearrangements of naphthyinitrenes: UV/Vis and IR spectra of azirines, cyclic ketenimines, and cyclic nitrile ylides. Journal of The American Chemical Society, 126 (1), 237-249. doi: 10.1021/ja038458z
2004
Journal Article
Macrocyclic systems containing 2,6,9-trioxabicyclo[3.3.1]-nona-3,7-dienes as chiral spacer groups: Synthesis, stereochemical features and preliminary complexation properties
Chebanov, V. A., Reidlinger, C., Kanaani, H., Wentrup, C., Kappe, C. O. and Kollenz, G. (2004). Macrocyclic systems containing 2,6,9-trioxabicyclo[3.3.1]-nona-3,7-dienes as chiral spacer groups: Synthesis, stereochemical features and preliminary complexation properties. Supramolecular Chemistry, 16 (2), 121-127. doi: 10.1080/10610270310001614197
2004
Journal Article
1H-1,3-Diazepines, 5H-1,3-diazepines, 1,3-diazepinones, and 2,4-diazabicyclo[3.2.0]heptenes
Reisinger, A., Koch, R., Bernhardt, P. V. and Wentrup, C. (2004). 1H-1,3-Diazepines, 5H-1,3-diazepines, 1,3-diazepinones, and 2,4-diazabicyclo[3.2.0]heptenes. Organic & Biomolecular Chemistry, 2 (8), 1227-1238. doi: 10.1039/b317099c
Funding
Supervision
Availability
- Emeritus Professor Curt Wentrup is:
- Not available for supervision
Supervision history
Completed supervision
-
2006
Doctor Philosophy
SYNTHESES AND REACTIONS OF IMINOPROPADIENONES, SYDNONES AND OXAZINONES
Principal Advisor
Other advisors: Professor Craig Williams
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2002
Doctor Philosophy
HETEROCYCLIC SYNTHESIS BASED ON IMINOPROPADIENONES
Principal Advisor
-
2002
Doctor Philosophy
SYNTHESIS AND CHARACTERISATION OF 1,3- and 1,4- DIAZEPINES AND DERIVATIVES
Principal Advisor
-
Doctor Philosophy
NITRENES REARRANGEMENTS: FORMATION OF REACTIVE INTERMEDIATES AND UNUSUAL MOLECULES
Principal Advisor
Other advisors: Professor Craig Williams
Media
Enquiries
Contact Emeritus Professor Curt Wentrup directly for media enquiries about:
- Organic reaction mechanisms
- Photochemistry
- Pyrolysis
- Reactive intermediates
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