Campus Directory: Peter Dibble

University of Lethbridge

Peter Dibble
Chemistry & Biochemistry
Office: E858 (University Hall)
Phone: (403) 329-2305
Fax: (403) 329-2057


B.Sc. (Applied Chemistry, Hons.), University of Waterloo; PhD (Organic Chemistry), University of Waterloo


Organic Synthesis, Applied organic spectroscopy, Isobenzofurans, Cyclophanes, Polycyclic aromatic hydrocarbons, Ring-chain tautomerism

Research Areas

Isobenzofurans, Cyclophanes, Ring-chain tautomerism, Theoretically interesting molecules, Molecular belts or cyclacenes, Molecular belts or cyclacenes

Selected Publications

"4,14:7,11-Diepoxy-2,9-propanonaphtho[1,2-f:5,6-f']diisoindole-1,3,8,10-tetrone,3a,4,7,7a,10a,11,14,14a-octahydro(2R,3aR,4S,7R,7aS,9R,10aR,11S,14R,14aS)-rel- (9CI), a cyclophane derived from naphtho[1,2-c:5,6-c]difuran", Michelle E. Thibault, Masood Parvez and Peter W. Dibble, Acta Cryst. E., in press.

"Furans and their Benzo Derivatives: Applications", Peter W. Dibble, Matthew Letts and Brian A. Keay, "Comprehensive Heterocyclic Chemistry III", 2008, Elsevier.

"1,3-Diphenylisobenzofuran", Rene´ T. Boere´,* Peter W. Dibble and Kristapher E. Fischer, Acta Cryst. (2008) E64, o686.

"Structures of the 2:1 adducts of benzyne with 2-methylanisole and benzene", C. O. Bender, R. T. Boeré, P. W. Dibble, R. T. McKay, Can. J. Chem., 2007, 85, 461-465.

"Diels-Alder Reactivity of Benzannulated Isobenzofurans as assessed by Density Functional Theory", Davor Margetic*, R. N. Warrener and Peter W. Dibble, Journal of Molecular Modeling, Springer, 13.01.2004, vol. 0, no. 2, pp. 87-93.

"Naphtho[l,2-c:5,6-c]difuran: reactive linker and cyclophane precursor", Taunia L. L. Closson, Sidney Manning, Michelle E. Thibault, and Peter W. Dibble*, J. Org. Chem. 2003, 68, 8373-8378.

"The synthesis and photochromic properties of molecules containing [e]- annelated dihydropyrenes. Two and three way pi-switches based on the dimethyldihydropyrene-metacyclophanediene valence isomerization"; Reginald H. Mitchell,* Timothy R. Ward, Yongsheng Chen, Yunxia Wang, S. Ananda Weerawarna, Peter W. Dibble, Michael J Marsella, Adah Almutairi, and Zhi-Qiang Wang; J. Am. Chem. Soc., 2003, 125, 2974-2988.

"Phenanthro[2,3-c]furan - A Stable Benzologue of Isobenzofuran with Greater Reactivity", Michelle Thibault, Laurie A. Pacarynuk, Taunia L. Closson and Peter W. Dibble*, Tetrahedron Lett, 2001, 42, 789-791.

"pi-Switches: Synthesis of Three-Way molecular Switches Based on the Dimethyldihydropyrene-Metacyclophanediene Valence Isomerization", Reginald H. Mitchell, Timothy R. Ward, Yunxia Wang and Peter W. Dibble, J. Am. Chem. Soc. 1999, 121, 2601-2602.

"Naphtho[1,2-c:5,6-c]difuran, a Stable Isobenzofuran Derivative", Daniel W. Yu, Kathryn E. Preuss, Paulette R. Cassis, Dontem Dejikhangsar and Peter W. Dibble, Tetrahedron Letters, 1996, 49, 8845-8848.

"Furans and Their Benzo Derivatives: Applications", Brian A. Keay and Peter W. Dibble, Comprehensive Heterocyclic Chemistry II, Volume 2, Chapter 8, pp. 395-436, Pergammon Press, Oxford, 1996.

"Steric and Electronic Effects in Imine/Hemiaminal Ring-Chain Tautomerism", Sean D. Derrick, Richard Boehme, Ken M. Wong, Frank Nemeth, Kelly Tanaka, Brian Rumberg, Richard A. Beekman and Peter W. Dibble, Tetrahedron, 1996, 52, 7679-7690.

"The Generation of Anthra [2,3-c]furan via Aromatic-Ring Homologation of Naphtho[2,3-c]furan", Noah P. W. Tu, Judy C. Yip and Peter W. Dibble, Synthesis, 1996, 77-81.

"Teraryls via Phenylenebis(isobenzofuran)s", Susan Leong-Neumann, Sean D. Derrick and Peter W. Dibble, Tetrahedron Lett. 1995, 36, 4181,

"High-pressure Intramolecular Diels-Alder Reactions of the Furan Diene", Brian A. Keay and Peter W. Dibble, Tetrahedron Lett. 1989, 30, 1045.

"The EI Mass Spectra of Isobenzofurans and Adducts Therefrom", Peter W. Dibble and Russell Rodrigo, Org. Mass. Spec. 1988, 30, 1045.

"1-Phenylisobenzofuran, 1-Phenylnaphtho[2,3-c]furan, 1-Phenylnaphtho[1,2-c]furans", James G. Smith, Deryn E. Fogg, Ian J. Munday, Richard E. Sandborn and Peter W. Dibble, J. Org. Chem. 1988, 53, 2942-2953.

"Polycyclic aromatic hydrocarbons via 1-(arylmethyl)isobenzo- and -naphtho[2,3-c]furans", James G. Smith, and Peter W. Dibble, J. Org. Chem., 2008, 53, 1841-1848.

"The preparation and reactions of naphtho[1,2-c]furan and naphtho[2,3-c]furan", James G. Smith, Richard E. Sandborn and Peter W. Dibble, J. Org. Chem. 1986, 51, 3762-3768.

"Ring-chain tautomerism of 1-hydroxyphthalans. An examination of structural effects", James G. Smith and Peter W. Dibble, Tetrahedron, 1984, 40, 1667-1672.

"Naphtho[1,2-c]furan and Naphtho[2,3-c]furan", James G. Smith and Peter W. Dibble, Chem. Comm., 1983, 1197.

"2-(Dimethoxymethyl)benzyl alcohol: a convenient isobenzofuran precursor", James G. Smith and Peter W. Dibble, J. Org. Chem., 1983, 48, 5361-5362.

Research Interests

I specialize in methods of generating a class of highly reactive organic molecules known as "isobenzofurans". These molecules are interesting for their electronic properties and are also very useful for the preparation of a huge number of interesting compounds. I apply this work to the preparation of liquid crystals, carcinogens, anti-tumour agents and brightly coloured fluorescers. Some of the molecules I make are interesting for another reason. These molecules exist in two forms in solution, something that is called a ring-chain tautomerism. I am studying a wide variety of these molecules in an effort to determine how certain molecular structural components influence the reactivity of groups elsewhere in the molecule.

Current Research and Creative Activity

TitleLocationGrant InformationPrincipal InvestigatorCo Researchers
Isobenzofurans Lethbridge, AB Natural Sciences and Engineering Research Council (NSERC), $30,000, 2004-09.

Peter Dibble, University of Lethbridge

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