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-c’]difuran.  This was used to make the molecule on the right, a pyrenophane.  It’s 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 René Boeré.

 

 

 

 

Dr. Dibble’s Publication List:

 

25)         “Synthesis and Characterization of 2,7-Di(tert-butyl)pyreno[4,5-c:9,10-c’]difuran and Derived Pyrenophanes”, David Franz, Steven J. Robbins, René T. Boeré and Peter W. Dibble*, J. Org. Chem, 2009, in press.

24)         “X-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 Derivative”, Steven J. Robbins, Michelle E. Thibault, Jason D. Masuda, David R. Ward, René T. Boeré and Peter W. Dibble, J. Org. Chem., 2009, 74, pp. 5192-5198.

 

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

 

22)         “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. (2008). E64, o1837.

 

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

 

20)         “1,3-Diphenylisobenzofuran”, Reneę T. Boereę,* Peter W. Dibble and Kristapher E. Fischer, Acta Cryst. (2008) E64,  o686.

 

19)         “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.

 

18)         “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.

 

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)        “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.

 

15)         “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.

 

14)         “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.

 

13)         “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.

 

12)         “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.

 

11)         “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.

 

10)         “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.

 

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

 

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

 

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

 

6)           “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.

 

5)           “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.

 

4)           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.

 

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

 

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

 

1)           “2-(Dimethoxymethyl)benzyl alcohol: a convenient isobenzofuran precursor”, James G. Smith and Peter W. Dibble, J. Org. Chem., 1983, 48, 5361-5362.