Welcome to the Research Website

of

Peter W. Dibble

Bringing you cooler molecules since 1987.

Contact information:

Department of Chemistry and Biochemistry

University of Lethbridge

Lethbridge  AB  Canada, T1K 3M4

Dibble@uleth.ca

Phone:  Office:  329-2305; Lab:  329-2308

 

The Molecular Hall of Phane

 

 

 

On the left is the X-ray structure of pyreno[4,5-c;9,10-cÕ]difuran.  This was used to make the molecule on the right, a pyrenophane.  ItÕs an example of a cyclophane:  molecules that have a flat aromatic portion linked across the ring by an aliphatic chain.  These were prepared by David Franz; X-ray structures by Steve Robbins and RenŽ BoerŽ.

 

 

 

 

Dr. DibbleÕs Publication List:

 

25)         ÒSynthesis and Characterization of 2,7-Di(tert-butyl)pyreno[4,5-c:9,10-cÕ]difuran and Derived PyrenophanesÓ, David Franz, Steven J. Robbins, RenŽ T. BoerŽ and Peter W. Dibble*, J. Org. Chem, 2009, in press.

24)         ÒX-ray Structures of Cyclophanes Derived from Naphtho[1,2-c:5,6-c]difuran and the Synthesis, Structure and Reaction Kinetics of its 1,3,6,8-Tetrasilylated DerivativeÓ, Steven J. Robbins, Michelle E. Thibault, Jason D. Masuda, David R. Ward, RenŽ T. BoerŽ and Peter W. Dibble, J. Org. Chem., 2009, 74, pp. 5192-5198.

 

23)         ÒStable phenylene- and biphenylenebis(isobenzofuran)s related to diphenylisobenzofuranÓ, Sheri A. Klassen, Richard Boehme, Sean D. Derrick, Klaus Moock, A. Elizabeth Baker, Deryn E. Fogg,  RenŽ T. BoerŽ and Peter W. Dibble, Can. J. Chem., 2009, 87, pp 738-744.

 

22)         Ò4,14:7,11-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]difuranÓ, Michelle E. Thibault, Masood Parvez and Peter W. Dibble, Acta Cryst. (2008). E64, o1837.

 

21)         ÒFurans and their Benzo Derivatives: ApplicationsÓ, Peter W. Dibble, Matthew Letts and Brian A. Keay, ÒComprehensive Heterocyclic Chemistry IIIÓ, 2008, Elsevier.

 

20)         Ò1,3-DiphenylisobenzofuranÓ, Rene« T. Boere«,* Peter W. Dibble and Kristapher E. Fischer, Acta Cryst. (2008) E64,  o686.

 

19)         ÒStructures of the 2:1 adducts of benzyne with 2-methylanisole and benzeneÓ, C. O. Bender, R. T. BoerŽ, P. W. Dibble, R. T.  McKay, Can. J. Chem., 2007, 85, 461-465.

 

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

 

17)         "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.

 

 16)        ÒThe synthesis and photochromic properties of molecules containing [e]- annelated dihydropyrenes. Two and three way pi-switches based on the dimethyldihydropyrene-metacyclophanediene valence isomerizationÓ; 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.

 

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

 

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

 

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

 

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

 

11)         ÒSteric and Electronic Effects in Imine/Hemiaminal Ring-Chain TautomerismÓ, 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.

 

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

 

9)           ÒTeraryls via Phenylenebis(isobenzofuran)sÓ, Susan Leong-Neumann, Sean D. Derrick and Peter W. Dibble, Tetrahedron Lett. 1995, 36, 4181,

 

8)           ÒHigh-pressure Intramolecular Diels-Alder Reactions of the Furan DieneÓ, Brian A. Keay and Peter W. Dibble, Tetrahedron Lett.  1989, 30, 1045.

 

7)           ÒThe EI Mass Spectra of Isobenzofurans and Adducts TherefromÓ, Peter W. Dibble and Russell Rodrigo, Org. Mass. Spec. 1988, 30, 1045.

 

6)           Ò1-Phenylisobenzofuran, 1-Phenylnaphtho[2,3-c]furan, 1-Phenylnaphtho[1,2-c]furansÓ, James G. Smith, Deryn E. Fogg, Ian J. Munday, Richard E. Sandborn and Peter W. Dibble, J. Org. Chem. 1988, 53, 2942-2953.

 

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

 

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

 

3)           ÒRing-chain tautomerism of 1-hydroxyphthalans. An examination of structural effectsÓ, James G. Smith and Peter W. Dibble, Tetrahedron, 1984, 40, 1667-1672.

 

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

 

1)           Ò2-(Dimethoxymethyl)benzyl alcohol: a convenient isobenzofuran precursorÓ, James G. Smith and Peter W. Dibble, J. Org. Chem., 1983, 48, 5361-5362.