Professor Curt Wentrup's research group is concerned with several areas of fundamental and applied chemistry:

(i) Medicinal and heterocyclic chemistry:1,3-diazepines; quinolones; others

(see several projects below).

(ii) Prebiotic and cosmological Chemistry

synthesis and chemistry of organic molecules of prebiotic (origin of life) interest, e.g. HN=CH-CN and H₂C=N-CN, and related molecules in interstellar space (J.Am.Chem.Soc. 1991, 113, 7261; New Scientist, 12 December 1992, p. 16)

(iii) Novel, unusual and reactive molecules

of theoretical significance, many discovered in our own lab, e.g. N₂S, S=C=C=S, R-CN-S, R-CN-N-R', nitrenes, carbenes, and cumulenes, R-N=C=C=C=O, RN=C=C=C=X. See e.g. J. Am. Chem.Soc. 1991, 113, 3130; 1996, 118, 5634; 1997, 119, 2819. Mini-Review: J. Phys. Org. Chem. 1998, 11, 350. J. Chem. Soc., Perkin Trans 2, 1999, 1683, 1869. J. Org. Chem. 1999, 64, 3608. J. Phys. Chem. A. 2000, 104.

(iv) Computational chemistry

ab initio calculations of molecular structure, spectra and energies. With Drs M. W. Wong and R. Koch. See e.g. J.Org.Chem. 1996, 61, 7022 and 6809; 1998, 63, 2619. J .Am. Chem. Soc. 1996, 118, 12598; 1998, 120, 1701, 2000, 122.

(v) Chemistry without solvents

gas phase pyrolysis reactions - including industrially important reactions. This is Green Chemistry . Numerous publications.

(vi) Photochemistry & spectroscopy at high and low temperatures:

NMR, IR, UV, ESR, and Mass spectrometries. Including considerable apparatus design and development. State-of-the-art spectrometers and cryostats for matrix isolation are available.

Project 1: Novel Cumulenes and Their Chemistry

The iminopropadienones, RN=C=C=C=O were first prepared and characterized in our laboratory, and although highly reactive, it is possible to isolate some of these derivatives and investigate their synthetic chemistry. Thus, the stable mesityl derivative gives rise to a number of novel heterocyclic compounds via nucleophilic addition, some of them of potential pharmaceutical interest. Further investigation of the preparative use of these and related reactions is required, as well as detailed mechanistic and low temperature spectroscopic studies of the formation and reactivity of the cumulenes. The production of novel Mesoionic Compounds based on RNCCCO cycloaddition chemistry is of much current interest, e.g. as shown in the scheme^#.

Recent publications from our group: Herve Bibas, Dan Moloney, Xuan Ye, John Andraos, Curt Wentrup* et al., Pure Appl. Chem.1995, 67, 749 and 1996, 68, 891. Chem. Eur. J. 1996, 2, 1318. J. Org. Chem. 1997, 62, 4240. J. Chem. Soc., Perkin Trans 2, 1999, 1087. J. Chem. Soc., Perkin Trans 1, 2000, 401.

Project 2: Diazepine Pharmaceuticals

Diazepines and in particular benzodiazepines are important drugs. We have in hand efficient methods of production of diazacycloheptatetraenes, substituted with CF₃ and other groups, that on reaction with nucleophiles are converted to stable diazepines. Currently, the introduction of fluorinated groups in pharmaceuticals is of much interest. The project involves the synthesis of diazepines, diazepinones, and their benzo analogs as well as fundamental mechanistic investigation of nitrene, carbene, and carbodiimide reactions as illustrated in the scheme^#.

Recent publications from our group: Richard Evans, Ales Reisinger, and Curt Wentrup*, J. Am. Chem. Soc. 1996, 118, 4009. J. Chem. Soc,. Chem. Commun.1996, 813. Pure Appl. Chem. 1997, 69, 847. J. Chem. Soc., Perkin Trans. 1, 1998, 2247. J. Am. Chem. Soc. 2000, 122.

Project 3: Novel Quinolone Antibiotics

The quinolones constitute a potent class of antibiotics (the first classes were penicillins, cephalosporins, aminoglycosides, and tetracyclines). Because of resistance, there is a constant need to develop new antibiotics and synthesize new types. We are developing new strategies for such syntheses, involving cyclization of ketene intermediates as shown in the example^#. This is based on the oxoketene-oxoketene and imidoylketene-oxoketenimine rearrangements discovered in our group, which are under continuing and intense investigation. Further developments into naphthyridone and quinazolinone chemistry are planned as new projects in the group.

Recent publications from our group: Belinda Fulloon, Venkat V. Ramana Rao, Curt Wentrup* et al., J. Org. Chem. 1996, 61, 1363; J. Am. Chem. Soc. 1995, 117, 9582, 1998, 120, 1701. Chem. Eur. J. 1997, 3, 237. JCS Perkin Trans. 1, 1998, 2583. J. Org. Chem. 1999, 64, 3608.