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c a l i f o r n i a ' s   c a p i t a l  u n i v e r s i t yspacer

spacerJohn D. Spence


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• Vita

• Research Group


Courses::Research Interests::Publications::Links


Contact Information


Professor of Chemistry


Mon 1:30-3:00 and Wed 1:30-3:00






Sequoia Hall Room 528 C


Department of Chemistry
CSU, Sacramento
6000 J Street
Sacramento, CA 95819

Courses ::

  • CHEM 124 Organic Chemistry Lecture II (Spring 2014)
  • CHEM 25 Organic Chemistry Laboratory (Spring 2014)
  • CHEM 24 Organic Chemistry Lecture I (Fall 2014)
  • CHEM 25 Organic Chemistry Laboratory (Fall 2014)








Research Interests ::

As a synthetic organic chemist research in my group is centered around two general areas (1) the syntheses and activation of enediyne pro-drugs and (2) the syntheses and properties of macrocycles related to porphyrins and calixarenes.  


1.  Design and Synthesis of Light Activated Enediyne Pro-Drugs.  Bergman and related cyclizations of enediynes to produce 1,4-phenyl biradicals have drawn interest for applications ranging from drug development to polymer chemistry and syntheses of carbon rich materials.  Cyclization may be initiated thermally or photochemically to produce highly reactive diradical intermediates which abstraction hydrogen atoms from an appropriate donor molecule.




We are currently developing highly conjugated arenediynes to explore the effect of extended conjugation on thermal and photochemical reactivity of the enediyne unit.  Some of the compounds we have synthesized are illustrated below.




2.  Synthesis of Azacalix[4]arenes.  We are interested in fine-tuning the properties of calixarenes by developing synthetic methods to systematically replace the bridging carbon atoms in these macrocycles with nitrogen atoms.  This substitution can have a profound effect on the electronic and physical properties of these macrocycles and offer new motifs for their functionalization.  The general structure of the azacalix[4]arene, in it's anticipated cone conformation, is shown below.



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Publications ::  Full CV
(undergraduate co-authors underlined)

21.  J. D. Spence, M. L. Lackie, N. A. Clayton, S. A. Toscano, M. A. Farmer, E. Popova, and M. M. Olmstead.  Syntheses, Structure, and Reactivity of Acyclic Enetriyne and Enetetrayne Derivatives.  Tetrahedron Letters, 2014, 55, 1569-1572.


20.  J. D. Spence, A. C. Rios, M. A. Frost, C. M. McCutcheon, C. D. Cox, S. Chavez, R. Fernandez, and B. F. Gherman.  Syntheses, Thermal Reactivities and Computational Studies of Aryl-Fused Quinoxalenediynes:  Effect of Extended Benzannelation on Bergman Cyclization Energetics.  Journal of Organic Chemistry, 2012, 77, 10329-10339.


19.  N. V. Korovina, M. L. Chang, T. T. Nguyen, R. Fernandez, H. J. Walker, M. M. Olmstead, B. F. Gherman and J. D. Spence.  Syntheses and Reactivity of Naphthalenyl-Substituted Arenediynes.  Organic Letters, 2011, 13, 3660-3663.

18.  K. V. Lawson, A. C. Barton, and J. D. Spence.  Synthesis of Diazacalix[8]arene and Triazacalix[12]arene Methyl Ethers via Intramolecular Aryl Amination.  Org. Lett. 2009, 11, 895-898.

17.  A. R. Urbach, C. J. Pursell, and J. D. Spence.  Supramolecular Chemistry:  A Senior Capstone Course.  J. Chem. Ed. 2007, 84, 1785-1787.

16.  J. D. Spence, A. E. Hargrove, H. L. Crampton, and D. W. Thomas.  Porphyrenediynes:  Synthesis and Cyclization of meso-Enediynylporphyrins.  Tetrahedron Lett. 2007, 48, 725-728.

15.   N. S. Mills, J. D. Spence and M. M. Bushey.  Capillary Electrophoresis Analysis of Substituted Benzoic Acids.  J. Chem. Ed. 2005, 82, 1226-1228.

14.  J. D. Spence, E. D. Cline, D. M. LLagostera and P. S. O’Toole.  Synthesis and Bergman Cyclization of a beta Extended Porphyrenediyne.  Chem. Commun. 2004, 180-181.

13.  T. D. Lash, M. A. Muckey, M. J. Hayes, D. Liu, J. D. Spence and G. M. Ferrence.  Regioselective Oxidation of Benzocarbaporphyrins with Ferric Chloride: A Facile Synthesis of Bridged [18]Annulene Ketals with Strong Absorptions in the Far Red and an Unexpected Halogenation Reaction at the Interior Carbon Atom.  J. Org. Chem. 2003, 68, 8558-8570.


12.  J. D. Spence, A. E. Raymond and D. E. Norton.  Condensations of N-Arylhydroxylamines for the Preparation of 5,5’-di-tert-butyl-2,2’-dihydroxydiphenylamine.  Tetrahedron Letters 2003, 44, 849-851.


11.  T. D. Lash, M. J. Hayes, J. D. Spence, M. A. Muckey, G. M. Ferrence and L. F. Szczepura.  Conjugated Macrocycles Related to the Porphyrins.  21.  Synthesis, Spectroscopy, Electrochemistry and Structural Characterization of Carbaporphyrins.  J. Org. Chem. 2002, 67, 4860-4874.


10.  T. D. Lash, M. L. Thompson, T. M. Werner and J. D. Spence.  Synthesis of Novel Pyrrolic Compounds from Nitroarenes and Isocyanoacetates Using a Phosphazene Superbase.  Synlett 2000 (2), 213-216.


9.  J. D. Spence and T. D. Lash.  Porphyrins with Exocyclic Rings.  Part 14.  Synthesis of Tetraacenaphtho-porphyrins, a New Family of Highly Conjugated Porphyrins with Record Breaking Long Wavelength Electronic Absorptions.  J. Org. Chem. 2000, 65,1530-1539.   

8.  D. K. Moss, J. D. Spence and M. H. Nantz.  Effects of Propargylic Substitution and Annelation on the Cycloaromatization of a Bicyclo[7.3.1] Enediyne.  J. Org. Chem. 1999, 64, 4339-4343.

7.  T. D. Lash, J. L. Romanic, M. J. Hayes and J. D. Spence.  Towards Hydrocarbon Analogues of the Porphyrins:  Synthesis and Spectroscopic Characterization of the First Dicarbaporphyrin.  J. Chem. Soc., Chem. Commun. 1999, 819-820.


6.  M. J. Hayes, J. D. Spence, and T. D. Lash.  Facile Oxidation of a Carbaporphyrin at the Internal Carbon Atom:  Synthesis of Novel Benzo[18]annulene Ketals.  J. Chem. Soc., Chem. Commun. 1998, 2409-2410.


5.  T. D. Lash, P. Chandrasekar, A. T. Osuma, S. T. Chaney, and J. D. Spence.  Porphyrins with Exocyclic Rings.  Part 13.  Synthesis and Spectroscopic Characterization of Highly Modified Porphyrin Chromophores with Fused Acenaphthylene or Benzothiadiazole Rings.  J. Org. Chem. 1998, 63, 8455-8469.

4.  M. H. Nantz, D. K. Moss, J. D. Spence, and M. M. Olmstead.  Actuating Cycloaromatization of a Bicyclo[7.3.1] Enediyne by Annelation, an Example of Inverse Dependence on Bridge Hybridization.  Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473.

3.  R. P. Balasubramaniam, D. K. Moss, J. K. Wyatt, J. D. Spence, A. Gee, and M. H. Nantz.  Methylation-Ring Opening of 3,3-Disubstituted 2,3-Epoxy Alcohols.  Synthesis of Chiral Quaternary Fragments for Assembly of Briaran Diterpenes.  Tetrahedron 1997, 53, 7429-7444.

2.  J. D. Spence, J. K. Wyatt, D. M. Bender, D. K. Moss and M. H. Nantz.  Stereogenic Propargylic Centers Via Base-Mediated Terminal Allene Isomerization.  J. Org. Chem. 1996, 61, 4014-4021.

1.  J. D. Spence, L. E. Lowrie and M. H. Nantz.  Cyclobutene Formation Accompanying an Intramolecular Lewis Acid-Promoted Spirocyclization of a Propargylic Silane.  Tetrahedron Letters 1995, 36, 5499-5502.

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Links ::


• American Chemical Society
• ACS Publications
• CSUS Research and Contract Admin
• Dreyfus Foundation
• Fisher Scientific
• Sigma Aldrich
• Porphyrin.Net
• Chemistry Departments in United States



• McMurry Text Website
• Spectroscopy Database
• The Basics of NMR
• ChemFinder



last updated: 07/1/2011



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