Richard P. Johnson

Richard Johnson

PROFESSOR
Emeritus
Office: Chemistry, Parsons Hall Rm W215, Durham, NH 03824
Pronouns: He/him/his

Richard Johnson is Professor Emeritus of Chemistry after serving as a UNH faculty member from 1985 – 2023.       

Google Scholar Profile:  Richard P Johnson - Google Scholar

Professor Johnson developed an early love for science, turning over rocks in search of odd bugs and snakes and mixing chemicals in his basement laboratory.  Foregoing a likely career in herpetology, he chose organic chemistry, inspired by his mentor Roger Hahn at Syracuse University. At UNH, he has taught undergraduate and graduate courses in organic chemistry and is most honored to have won the UNH College of Engineering and Physical Sciences Outstanding Faculty Teacher award in 2006. His research interests lie in the broad field of physical organic chemistry, with emphasis on reaction mechanisms, pericyclic reactions, synthesis of novel organic structures, and applications of computational chemistry.  With support from NSF, his group has used high level theory as a tool to understand complex chemistry and to demonstrate the existence of seemingly impossible reactive intermediates,  including 1,2-cyclobutadiene, trialene and trans-benzene. The intramolecular diyne + yne Diels-Alder cycloaddition, discovered at UNH in 1997, is now a widely applied reaction in organic synthesis. His group developed synthetic routes to 1,2-cyclohexadiene and 1,2,3-cyclohextriene,  novel structures that are now being used in natural product synthesis. More recently, his group has studied the rearrangements and synthesis of aromatic compounds through carbocation intermediates. One recent discovery is a short and efficient route to the triangulene ring system. [https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201907226]  At last count, his research group graduated 36 Ph.D. or M.S. students and 24 B.S. Thesis students.  Professor Johnson  still views science as a process of turning over rocks to see what is underneath. There are few things better in life than the thrill of scientific discovery.

Among professional activities, Professor Johnson has served on the ACS Petroleum Research Fund Advisory Board,  the Graduate Record Exam Chemistry Committee, as Program Chair of the Reaction Mechanisms Conference,  as  Associate Editor of the Journal of Physical Organic Chemistry and as Co-Chair of the 2019 Gordon Research Conference in Physical Organic Chemistry. From 2014 – 2016, he served as a "rotator" Program Officer in the Chemistry Division of the National Science Foundation. He continues a part time appointment with NSF, working primarily in the CCI and CSDM-B Programs.

 

Selected Publications

Carter J. Holt, Katelyn Wentworth and Richard P. Johnson*, "A Short and Efficient Synthesis of the [3]Triangulene Ring System", Angewandte Chemie201958, 15793-15796.

https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201907226

Sarah L. Skraba-Joiner, Carter J. Holt and Richard P. Johnson* "Acid Catalyzed Rearrangements in Arenes:Interconversions in the Quaterphenyl Series",  Beilstein J. Org. Chem. 2019, 15, 2655-2663.

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-15-258.pdf

Kyle D. Reichl, Michael J. Smith, Min K. Song, Richard P. Johnson, and John A. Porco Jr.* “Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition–Cyclization Cascade”,Journal of the American Chemical Society 2017, 139 (40), pp 14053–14056. http://pubs.acs.org/doi/abs/10.1021/jacs.7b09265

Sarah L. Skraba-Joiner, Jeffrey W. Brulet, Min K. Song and Richard P. Johnson* “Acid Catalyzed Skeletal Rearrangements in Arenes: Aryl vs. Alkyl Ring Pirouettes in Anthracene and Phenanthrene”, Journal of Organic Chemistry, 2017, 82 (24), pp 13076–13083. http://pubs.acs.org/doi/10.1021/acs.joc.7b02058

Sarah L. Skraba-Joiner, Richard P. Johnson* and Jay Agarwal, “Dehydropericyclic Reactions: Symmetry Controlled Routes to Strained Reactive Intermediates”, Journal of Organic Chemistry, 2015, 80 (23), pp 11779–11787  http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b01488  This was an invited paper to commemorate “50 Years of the Woodward-Hoffmann Rules”.

Tian Qin,  Sarah L. Skraba-Joiner,  Zeinab G. Khalil,  Richard P. Johnson, Robert J. Capon, and John A. Porco, Jr.*  “Atropselective Syntheses of (-) and (+) Rugulotrosin A Utilizing Point-to-Axial Chirality Transfer” Nature Chemistry 2015,  7, 234–240.   doi:10.1038/nchem.2173

http://www.nature.com/nchem/journal/vaop/ncurrent/full/nchem.2173.html

Rajesh Thamatam, Sarah L.  Skraba and Richard P. Johnson*, "Scalable synthesis of quaterrylene:  1H NMR characterization as its oxidative dication", Chemical Communications, 2013, 49, 9122-9124. http://pubs.rsc.org/en/content/2013/cc/c3cc46270f  This work has now been patented, commercialized and Sigma-Aldrich is now selling quaterrylene at $10/mg.

Katharine J Cahill, and Richard P. Johnson*,  Beyond Frontier Molecular Orbital Theory: A Systematic Electron Transfer  Model (ETM) for Polar Bimolecular Organic Reactions,  J. Org. Chem. 2013, 78, 1864 – 1873.    This was an invited paper for the Howard Zimmerman Memorial Edition of  JOC. http://pubs.acs.org/doi/abs/10.1021/jo301731v

Sarah M. Skraba and Richard P. Johnson*, A Computational Model for the Dimerization of Allene, J. Org. Chem., 2012, 77, 11096-11100.    http://pubs.acs.org/doi/abs/10.1021/jo302176k

Aida Ajaz, Erin C. McLaughlin, Sarah L. Skraba, Rajesh Thamatam, and Richard P. Johnson* , Phenyl Shifts in Substituted Arenes via Ipso Arenium Ions,  J. Org. Chem., 2012, , 77, 9487-9495. http://pubs.acs.org/doi/abs/10.1021/jo301848g

Aida Ajaz, Alexander Z. Bradley, Richard C. Burrell, William Hoi Hong Li, Kimberly J. Daoust, Laura Boddington Bovee, Kenneth J. DiRico, and Richard P. Johnson*, Concerted vs. Stepwise Mechanisms in Dehydro Diels-Alder Reactions J. Org. Chem. 2011, 76, 9320-9328. http://pubs.acs.org/doi/abs/10.1021/jo201567d

Richard P. Johnson, Dehydropericyclic Routes to Reactive Intermediates, J. Phys. Org. Chem. 2010, 23,  283-292. http://onlinelibrary.wiley.com/doi/10.1002/poc.1656/abstract

Hee Yeon Cho, Aida Ajaz, Dibya Himali, Prashant Waske and Richard P. Johnson*  Microwave Flash Pyrolysis J. Org. Chem. 2009, 74, 4137-4142. http://pubs.acs.org/doi/abs/10.1021/jo900245v

Kimberly J. Daoust, Susanna M. Hernandez, Kaleen M. Konrad, Iain D. Mackie, James Winstanley Jr. and Richard P. Johnson*   “Strain Estimates for Small-Ring Cyclic Allenes and Butatrienes”  J. Org. Chem. 2006, 71, 5708 – 5714.  http://pubs.acs.org/doi/abs/10.1021/jo060698k

John E. Mabry and Richard P. Johnson "Beyond the Brown Rearrangement:  A Trialene Mechanism for Long Range Carbon Automerization in Conjugated Polyynes",  J. Am. Chem. Soc., 2002, 124, 6497 - 6501http://pubs.acs.org/doi/abs/10.1021/ja0260115

Alexander Z. Bradley, Martin G. Kociolek and Richard P. Johnson , "Conformational Selectivity in the  Diels-Alder Cycloaddition:   Predictions for Reactions of  s-trans-1,3-Butadienes " J. Org. Chem.  2000, 65,  7134 - 7138.  https://pubs.acs.org/doi/abs/10.1021/jo000916o

Alexander Z. Bradley and Richard P. Johnson*,  "Thermolysis of 1,3,8-Nonatriyne: Evidence for Intramolecular Cycloaromatization to a Benzyne Intermediate",   J. Am. Chem. Soc.1997, 119,  9917 - 9918. https://pubs.acs.org/doi/abs/10.1021/ja972141f

Richard P. Johnson* and Kimberly J. Daoust, "Electrocyclic Ring Opening Modes of Dewar Benzenes:  Ab Initio Predictions for Möbius Benzene and trans-Dewar Benzene as New C6H6 Isomers", J. Am. Chem. Soc.1996, 118,  7381 - 7385.  https://pubs.acs.org/doi/abs/10.1021/ja961066q

Richard C. Burrell, Kimberly J. Daoust,  Alexander Z. Bradley, Kenneth J. DiRico and Richard P. Johnson* "Strained Cyclic Cumulene Intermediates in  Diels-Alder Cycloadditions of Enynes and Diynes", Journal of the American Chemical Society, 118,  4218 - 4219 (1996).  https://pubs.acs.org/doi/10.1021/ja9601144

Richard P. Johnson* and Kimberly J. Daoust, "Interconversions of Cyclobutyne, Cyclopentyne, Cyclohexyne and Their Corresponding Cycloalkylidenecarbenes"  Journal of the American Chemical Society  117, 362–367 (1995). https://pubs.acs.org/doi/pdf/10.1021/ja00106a040

Manli Zheng,  Kenneth J. DiRico, Mary M. Kirchhoff,  Kristine Phillips,  Lisa M. Cuff and Richard P. Johnson*,  "Photorearrangements of Acyclic Conjugated Enynes:  A Photochemical Analogue of the Bergman Rearrangement"  Journal of the American Chemical Society115, 12167–12168 (1993). https://pubs.acs.org/doi/abs/10.1021/ja00078a066

W. C. Shakespeare and R. P. Johnson*, "1,2,3–Cyclohexatriene and Cyclohexen–3-yne: Two New Highly Strained C6H6  Isomers", J. Am. Chem. Soc.,112, 8578 – 8579 (1990). https://pubs.acs.org/doi/pdf/10.1021/ja00179a050       Note:     This work was featured in Chemical and Engineering News.

J. E. Chateauneuf*, R. P. Johnson* and M. M. Kirchhoff, "Absolute Kinetics of Dichlorocarbene in Solution", J. Am. Chem. Soc., 112, 3217 – 3218 (1990). https://pubs.acs.org/doi/abs/10.1021/ja00164a056

R. P. Johnson, "Strained Cyclic Cumulenes", Chem. Rev., 89, 1111 – 1124  (1989). https://pubs.acs.org/doi/abs/10.1021/cr00095a009

J. D. Price and R. P. Johnson*,  "Small-Ring Cyclic Cumulenes:  Synthesis of a Kinetically Stable 1,2- Cyclooctadiene", J.D. Price and R.P. Johnson*, Tetrahedron Letters  27, 4679 – 4682 (1986).

M. W. Klett and R.P. Johnson*, "Cumulene Photochemistry:  Photorearrangements of Tetraphenyl and Triphenyl C3 Isomers", J. Am. Chem. Soc., 1985,  107, 3963-3971

T. J. Stierman and R.P. Johnson*, "Cumulene Photochemistry:  Singlet and Triplet Photorearrangements of 1,2-Cyclononadiene", J. Am. Chem. Soc., 107, 3971-3980 (1985).

R. O. Angus, Jr. and R. P. Johnson*, "Small-Ring Cyclic Cumulenes:  The Structure and Energetics of Cyclic Butatrienes and the Synthesis of 1,2,3-Cyclononatriene", J. Org. Chem., 49, 2880-2883 (1984).

R.O. Angus, Jr. and R.P. Johnson*, "A Butatriene Cycloaddition Equivalent Approach to the Multiple Linear Homologation of Six- Membered Rings and the Synthesis of Benzocyclobutenes", J. Org. Chem., 48, 273-277 (1983).

M. W. Schmidt, R. O. Angus, Jr. and R. P. Johnson*, "Small-Ring Cyclic Allenes:  An Ab Initio Study of 1,2-Cyclohexadiene", J. Am. Chem. Soc., 104, 6838-6839 (1982).

E. Haselbach*, L. Neuhaus, R. P. Johnson, K. N. Houk and M. N. Paddon- Row, " Orbital Interactions in Mobius-Type Molecules as Studied by Photoelectron Spectroscopy", Helv. Chim. Acta, 65, 1743-1751 (1982).

H. E. Zimmerman* D. Armesto, M. G. Amezua, T. P. Gannett and R. P. Johnson, "Unusual Organic Photochemistry Effected by Cyano and Methoxy Substitution.  Exploratory and Mechanistic Organic Photochemistry", J. Am. Chem. Soc. 101, 6367-6383 (1979).

L. N. Domelsmith, P. D. Mollere, K. N. Houk*, R.C. Hahn* and R.P. Johnson, "Photoelectron and Charge-Transfer Spectra of Benzobicycloalkenes.  Relationships Between Through-Space Interactions and Reactivity", J. Am. Chem. Soc. 100, 2959-2965 (1978).  

R.C. Hahn* and R. P. Johnson, "Effect of a Nitro Substituent on Di-π- methane Rearrangement of Benzonorbornadiene and its [3.2.1] Homolog", J. Amer. Chem. Soc. 99, 1508-1513 (1977).

R.C. Hahn* and R. P. Johnson, "Photochemical Rearrangements of Some Benzo (C9H10) Isomers", J. Amer. Chem. Soc., 98, 2600-2604 (1976).

R.C. Hahn* and R. P. Johnson, "A Facile Entry into the Benzo[7,8]- bicyclo[4.2.1]nonane System", Tetrahedron Letters, 2149-2152 (1973).