The Dalton Gang at Temple University

Curriculum Vitae

David Robert Dalton

EDUCATION and POSITIONS HELD:

Northwestern University, Evanston, IL, B.A. (with Honors), 1957.

University of California, Los Angeles, CA, Ph.D., 1962.

1962-1964 Research Chemist, Monsanto Research Corporation Dayton Laboratories. A division of the Monsanto Company (acquired by Bayer in 2018).

1964-1965 Instructor and National Institutes of Health, Postdoctoral Fellow, The Ohio State University, Columbus, Ohio

1965 – present, Temple University , Philadelphia, PA.

VISITING PROFESSORSHIPS:

1972-1973 Israel Institute of Technology (Technion), Haifa, Israel

1976-1977 Yale University, New Haven, Connecticut

1988-1989 Bryn Mawr College, Bryn Mawr, Pennsylvania

1992 Visiting Master Teacher in Residence, Clemson University, Clemson, South Carolina.

NAME SPECIAL AWARDS RECEIVED FOR TEACHING EXCELLENCE:

PUBLICATIONS:

BOOKS PUBLISHED OR IN PRESS:

  • D. R. Dalton, The Alkaloids: The Fundamental Chemistry – A Biogenetic Approach. M. Dekker, Inc., New York (1979).
  • M. T. Yip and D. R. Dalton, Organic Chemistry in The Laboratory. D. van Nostrand Company, New York, (1979).
  • Dalton, David R. Foundations of Organic Chemistry: Unity and Diversity of Structures, Pathways, and Reactions, Wiley-VCH Publishers , New York (2011). ISBN 978-0-470-47908-7.
  • Dalton, David R. The Chemistry of Wine. Oxford University Press , New York (2017), ISBN 978-0-19-068719-9.
  • Dalton, David R. Foundations of Organic Chemistry: Unity and Diversity of Structures, Pathways, and Reactions, 2nd edition. Wiley-VCH Publishers, New York (2020). Print ISBN: 978-1-119-65642-5 and eBook ISBN: 978-1-119-65643-2.

RESEARCH ARTICLES PUBLISHED OR IN PRESS:

  • Summerbell, R.K.; Berlingame, A.L.; Dalton, D.R.; Dalton, C.K. “The Dimethyl-p-dioxanes and the 2,5-Dibutyl-p-dioxanes,” J. Org. Chem. 1962 , 27, 4365 (doi:10.1021/jo01059a055).
  • Dalton, D.R.; Cava, M.P.; Buck, K.T. “Hindered Rotation in l-Benzyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines”, Tetrahedron Lett. 1965, 6 2687 (10.1016/S0040-4039(01)99526-7).
  • Cava, M.P.; Wilkins, Jr., C.K.; Dalton, D.R.; Bessho, K. “A New Isoquinuclidine Synthesis. A New Route to dl-Dioscorone”, J. Org. Chem. 1965, 30, 3772 (doi:10.1021/jo01022a042).
  • Shamma, M.; Dudock, B.S.; Cava, M.P.; Rao, K.V.; Dalton, D.R.; DeJongh, D.C.; Schraeder, S.R. “Revised Structures of Hernandezine and Thalsimine. Mass Spectrometry of a Bisbenzylisoquinoline Alkaloid”, Chemical Communications 1966, 7 (doi:10.1039/C19660000007).
  • Cava, M.P.; Dalton, D.R. “An Improved Synthesis of dl-Anonaine”, J. Org. Chem. 1966, 31, 1281 (doi:10.1021/jo01342a507).
  • Dalton, D.R.; Hendrickson, J.B.; Jones, D.G. “An Improved Procedure for the Preparation of Bromohydrins”, Chemical Communications 1966, 591 (doi:10.1039/C19660000591).
  • Fraenkel, G.; Cava, M.P.; Dalton, D.R. “Hindered Rotation in l-Benzyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines”, J. Am. Chem. Soc. 1967, 89, 329 (doi:10.1021/ja00978a027).
  • Dalton. D.R.; Jones, D.G. “Halohydrin Formation in Dimethyl Sulfoxide”, Tetrahedron Lett. 1967, 8, 2857 (doi:10.1016/S0040-4039(00)90878-5).
  • Dalton, D.R.; Liebman, S.A.; Waldman, H.; Sheinson, R.S.”ESR Detection of the Diphenylmethyl Radical”, Tetrahedron Lett. 1968, 9, 145 (doi:1016/S0040-4039(00)75576-6).
  • Dalton, D.R.; Dutta, V.P.; Jones, D.G. “Bromohydrin Formation in Dimethyl Sulfoxide”, J. Am. Chem. Soc. 1968, 90, 5498 (doi:10.1021/ja01022a030).
  • Dalton, D.R.; Liebman, S.A. “Electron Spin Resonance Studies On Neutral Hydrocarbon Radicals”, J. Am. Chem. Soc. 1969, 91, 1194 (doi:10.1021/ja01033a027).
  • Dalton, D.R.; Liebman, S.A. “Thermal and Photolytic Decomposition of Diarylmethylenetriphenylphosphazines and Diaryldiazomethanes”,Tetrahedron 1969 ,25, 3321 (doi:10.1016/S0040-4020(01)82865-9).
  • Hendrickson, J.B.; Alder, R.W.; Dalton, D.R.; Hey, D.G. “Some Approaches to Total Synthesis of Lycorine”, J. Org. Chem. 1969, 34, 2667 (doi:10.1021/jo01261a040).
  • Dalton, D.R.; Ramey, K.C.; Gisler, Jr., H.J.; Lendvay, L.J.; Abraham, A. “Hindered Rotation in Substituted 1,2,3,4-Tetrahydro-6,7-dimethyoxyisoquinolines”, 1969, 91, 6367 (doi: 10.1021/ja01051a031.
  • Charleston, B.S.; Dalton, C.K.; Washburne, S.S.; Dalton, D.R; Schraeder, S.R. “Chemistry of the Vinyl Cation – The Addition of DC1 to Allene”,Tetrahedron Lett. 1969, 10, 5147 (doi:10.1016/S0040-4039(01)88908-5).
  • Dalton, D.R.;Smith, Jr., R.C.; Jones, D.G. “Bromoformate Formation in Dimethylformamide”, Tetrahedron 1970, 26, 575 (doi:10.1016/S0040-4020(01)97850-0).
  • Dalton, D.R.; Liebman, S.A. “Electron Spin Resonance Studies on Neutral Hydrocarbon Radicals – Substituent and Isotope Effects”,Tetrahedron 1970, 26, 3265 (doi:10.1016/S0040-4020(01)92905-9).
  • Dalton, D.R.; Dutta, V.P. “Bromohydrin Formation in Aqueous Dimethyl Sulphoxide; Electronic and Steric Effects”, J. Chem. Soc. (B) 1971, 85 (doi:10.1039/J29710000085).
  • Dalton, D.R.; Miller, S.I.; Dalton, C.K.; J.K. Crelling, J.K.; “The Synthesis of Nitrobenzyl)-4-hydroxy-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline. Synthesis of 1-Substituted-4-oxygenated-1,2,3,4-tetrahydroisoquinolines”, Tetrahedron Lett. 1971, 12, 575 (doi:10.1016/S0040-4039(01)96500-1).
  • Dalton, D.R.; Rodebaugh, R.K.; Jefford, C.W. “Bromohydrin Formation in Dimethyl Sulfoxide. V. The Reaction of Norbornene”, J. Org. Chem. 1972, 37, 362 (doi:10.1021/jo00968a006).
  • Dalton, D.R.; Davis, R.M. “Bromohydrin Formation in Dimethyl Sulfoxide. The Reaction of Conjugated Dienes”,Tetrahedron Lett. 1972, 13, 1057 (doi:10.1016/S0040-4039(01)84507-X).
  • Dalton, D.R.; Abraham, A.A. “The Synthesis of Aporphine Alkaloids III. Steric Effects in the Pschorr Cyclization”, Synthetic Communications 1972, 2, 303 (doi:10.1080/00397917208061985).
  • Dalton, D.R.; Foley, H.G.; Trueblood, K.N.; Murphy, M.R.. “Unusual Nitrones” Tetrahedron Lett. 1973, 14, 779 (doi:10.1016/S0040-4039(01)95710-7).
  • Liebman, S.A.;Dalton, D.R.;Knudsen, T.;Underwood, G. “Stereochemistry of the Diphenylmethyl Radical”, J. Mag. Res. 1973, 10, 85 (doi:10.1016/0022-2364(73)90238-2).
  • Foley, H.G.; Dalton, D.R. “A Convenient, Neutral Conversion of Aldoximes to Nitriles at Low Temperature”, Chemical Communications 1973,17, 628 (doi:10.1039/C39730000628).
  • Dalton, D.R.; Foley, H.G. “O-Carbamoyl Oximes”, J. Org. Chem. 1973, 38, 4200 (doi:10.1021/jo00963a022).
  • Foley, H.G.; Dalton, D.R. “A General, Neutral Beckmann Rearrangement of Ketoximes. The Isolation of an Intermediate”, Synthetic Communications 1974 4, 251 (doi:10.1080/00397917408062082).
  • Amar, F.; Dalton, D.R.; Eisman, G.; Haugh, M.J. “The Uncatalyzed Gas Phase Hydrochlorination of Alkenes I. Propene and Isobutylene”, Tetrahedron Lett. 1974, 15, 3033 (doi:10.1016/S0040-4039(01)91814-3).
  • Amar, F.; Dalton, D.R.; Eisman, G.; Haugh, M.J. “The Uncatalyzed Gas Phase Hydrochlorination of Alkenes II. Allene”, Tetrahedron Lett. 1974,15, 3037 (doi:10.1016/S0040-4039(01)91815-5).
  • Haugh, M.J.; Dalton, D.R. “The Gas Phase Addition of Hydrogen Chloride to Propylene”, J. Am. Chem. Soc. 1975 , 97, 5674 (doi:10.1021/ja00853a005).
  • Krow, G.; Damodaran, M.; Michner, M.; Miller, S.I.; Dalton, D.R. “Nonsymmetric 9-Phenanthrylamines. An Improved Synthetic Procedure to a Useful Synthon”, Synthetic Communications 1976, 6, 261 (doi:10.1080/00397917608063520).
  • Scott, A.I.; Kang, J.; Dalton, D.R.; Chang, S.K. “Mechanism of Action of Coenzyme B12. An Overall Anionic Mechanism for Carbon-Skeleton Rearrangement in a Model Reaction”, J. Am. Chem. Soc. 1978, 100, 3603 (doi:10.1021/ja00479a055).
  • Langman, A.W.;Dalton, D.R. “Bromohydrins from Alkenes and N-Bromosuccinimide in Dimethyl Sulfoxide: erythro-2-Bromo-1,2-Diphenylethanol”, Organic Synthesis 1979 59 16 (doi: 10.15227/orgsyn.059.00160).
  • Washburne, S.S.;Dalton, D.R. “An Analogy for Quantization of Energy Levels.” J. Chem. Educ. 1980, 57, 200 (doi: 10.1021/ed057p200.3).
  • Chackalamannil, S.; Dalton, D.R. “The Synthesis of erythro and threo-N-methyl 7- Hydroxy-1,2,9,10-tetramethoxyaporphine”, Tetrahedron Lett. 1980, 21 2029 (doi:10.1016/S0040-4039(00)71477-8).
  • Tierney, J.; Dalton, D.R. “A Homemade High Pressure Gas Cell”, J. Chem. Educ. 1981, 58, 813 (doi:10.1021/ed058p813).
  • Wert, K.L.; Chackalamannil, S.; Miller, E.; Dalton, D.R.; Zacharias, D.E.; Glusker, J.P. “Hoffmann Degradation of á-Hydroxy Ammonium Salts. alpha- and beta- Hydroxylaudanosine, 7-Hydroxyglaucine, and 13-Hydroxyxylopinine”, J. Org. Chem. 1982, 47, 5141 (doi:10.1021/jo00147a020).
  • Costello, F.; Dalton, D.R.; Poole, J.A. “Hydrochlorination of Alkenes. 2. Reactions of the Gases Hydrogen Chloride and 2-Methylpropene”, J. Phys. Chem. 1986, 90, 5352 (doi:10.1021/j100412a091).
  • Tierney, J.; Costello, F.; Dalton, D.R. “Hydrochlorination of Alkenes. 3. Reactions of the Gases Hydrogen Chloride and (E)- and (Z)-2-Butene”, J. Org. Chem. 1986, 51, 5191 (doi:10.1021/jo00376a026).
  • Doshi, H.; Cardis, A.B.; Crelling, J.K.; Miller, S.I.; Dalton, D.R.; Zacharias, D.E.; Glusker, J.P. “Hoffman Degradation of á-Hydroxy Ammonium Salts. II. 4-Hydroxybenzylisoquinolines and 4-Hydroxyaporphines”, J. Org. Chem. 1987, 52, 2604 (doi:10.1021/jo00388a053).
  • Schnur, D.M.; Dalton, D.R. “MM2 Force Field Parameters for Oximes”, J. Org. Chem. 1988, 53, 3313 (doi:10.1021/jo00249a033).
  • Schnur, D.M.; Yuh, Y.H.; Dalton, D.R. “A Molecular Mechanics Study of Amide Conformations,” J. Org. Chem. 1989, 54, 3779 (doi:10.1021/jo00277a008).
  • Eshraghi, J.; Longo, J.; Dalton D.R.; Harrington, G.W. “An Unusual Ring Contraction in the Formation of N-Nitrosohexamethyleneimine and N- Nitrosopiperidine from Tolazamide”, Japanese J. Cancer Res. (Gann) 1990, 81, 324 (doi:10.1111/j.1349-7006.1990.tb02570.x).
  • Mascavage, L.M.; Chi, H.; La S.; Dalton, D.R. “Surface-Catalyzed Hydrochlorination of Alkenes. The Reaction of the Gases Hydrogen Chloride and 1,3-Butadiene”, J. Org. Chem. 1991, 56, 595 (doi:10.1021/jo00002a021).
  • Mascavage. L.M.; Dalton, D.R. “Surface Catalyzed Hydrochlorination of 1,3-Butadiene”, Tetrahedron Lett. 1991, 32, 3461 (doi:10.1016/0040-4039(91)80806-H).
  • Kao, B.-C.; Doshi, H.; Reyes-Rivera, H.; Titus, D.D.; Yin, M.; Dalton, D.R.
    “3-Substituted 2-Pyridinecarbaldoximes”, J. Heterocyclic Chem. 1991, 28, 1315 (doi:10.1002/jhet.5570280525).
  • Grant, A.D.; Zacharias, D.E.; Mascavage, L.M.; Kemmerer, G.E.; Dalton, D.R. “Chloromethylation of Codeine. Isolation of a Quaternary Iodide”, J. Heterocyclic Chem. 1993, 30, 553 (doi:10.1002/jhet.5570300250).
  • Jasmin, S.; Dalton, D.R.; Carroll P.J.; Kao, B.C. “The Synthesis and Spontaneous Resolution of 2-(3-Thioxothiazolidin-3-yl)thiazole.” J. Heterocyclic Chem. 1994 31, 1079 (doi:10.1002/jhet.5570310464).
  • Mascavage, L.M.; Zhang, F.; Dalton, D.R. “The Reaction of the Gases Hydrogen Chloride and 2-Butyne.” J. Org. Chem. 1994, 59, 5048 (doi:10.1021/jo00096a058).
  • Reyes-Rivera, H.M.; Hutchins, R.O.; Dalton, D.R. “2-Carbaldoximes of Pyridine 4- and 5-Carboxylic Acids.” J. Heterocyclic Chem. 1995, 32, 665 (doi:10.1002/jhet.5570320248).
  • Huang, Y.; Dalton D.R.; Carroll, P.J. “The Efficient, Enantio-selective Synthesis of Aza Sugars from Amino Acids. 1. The polyhydroxylated Pyrrolidines”. J. Org. Chem. 1997,62, 372 (10.1021/jo962028s).
  • Huang, Y.; Sonnet, P.E.; Carroll, P.J.; Dalton, D.R. “Diastereoselective Diels-Alder Reactions. The Role of the Catalyst.”,Tetrahedron Lett. 2000 , 41, 2519 (doi:10.1016/S0040-4039(00)00241-0).
  • Mascavage, L.M.; Lu, Q.; Vey, J.; Dalton D.R.; Carroll, P.J. “Enantioselective Synthesis of Aza Sugars from Amino Acids. 2. The 3-Hydroxy-2-hydroxymethylpyrrolidines.” J. Org. Chem. 2001,66, 3621 (doi:10.1021/jo001736h).
  • Huang, Y.; Sonnet, P.E.; Dalton, D.R. “Diasteroselective Diels-Alder Reactions. The Role of the Catalyst.2.” Archive for Organic Chemistry (ARKIVOC), 2001 : Part (vi) Commemorative Issue in Honor of Prof. Rudolph A. Abramovitch… ARKAT-USA :for the article itself, please click here (doi:10.3998/ark.5550190.0002.606).
  • Wilson, M.L.; Dalton, D.R.; Carroll, P.J. “Decoration of the Aromatic Ring of Dihydrocodeinone (Hydrocodone) and 14-Hydroxydihydrocodeinone (Oxycodone)”. J. Org. Chem. 2005, 70, 6492 (10.1021/jo050264+).
  • Mascavage,L.M.; Wilson M.L.; Dalton, D.R. ” Syntheses of Morphine and Codeine (1992 – 2002): Templates for Exploration of Synthetic Tools.” Current Organic Synthesis 2006 , 3 99.
  • Mascavage, L.M.; Sonnet P.E.; Dalton, D.R. “On the Surface-Catalyzed Reaction between the Gases 2,2-Dimethylpropanal and Methanamine. Formation of Active-Site Imines.” J. Org. Chem. 2006, 71 , 3435 (doi:10.1021/jo052503z).
  • Sonnet, P.E.; Mascavage L.M.; Dalton, D.R. “The First Steps. The Attack on the Carbonyl Carbon of Pyridoxal Cofactor in Pyridoxal- Dependent Enzymes.” , Bioorg. Med. Chem. Lett. 2008,18, 744 (doi:10.1016/j.bmcl.2007.11.051).
  • Mascavage, L.M.; Zhang-Plasket, F.; Sonnet, P.E.; Dalton, D.R. “Gas phase surface-catalyzed HCl addition to vinylacetylene: motion along a catalytic surface. Experiment and theory.” Tetrahedron 2008 , 64, 9357 (doi:10.1016/j.tet.2008.07.081) .
  • Mascavage, L.M.; Tierney, J.;Sonnet, P.E.; Dalton, D.R. “The Hoffmann-Schiff dichotomy:on the reaction between chloral and amines” Archive for Organic Chemistry (ARKIVOC), 2010 : Commemorative Issue in Honor of Dr. Bruce E. Maryanoff and Dr. Cynthia A. Maryanoff ARKAT-USA : 2010 278. For the article itself, please click here (doi:10.3998/ark.5550190.0011.819).
  • Judge, E.J.; Brady, J.J.; Dalton. D.R.; Levis, R.J. “Analysis of Pharmaceutical Compounds from Glass, Fabric, Steel, and Wood Surfaces at Atmospheric Pressure Using Spatially Resolved Nonresonant Femtosecond Laser Vaporization Electrospray Mass Spectrometry” Anal. Chem. : 2010 , 82 , 3231 (doi:10.1021/ac902880q).
  • Mascavage, L.M.; Sonnet, P.E.; Dalton, D.R. “Surface-Catalyzed Reaction between the Gases Hydrogen Chloride and Isoprene” ACS Earth Space Chem. 2017 3 , 122 (doi:10.1021/acsearthspacechem.7b00009).

    • PATENTS

    • D. R. Dalton, Y. Huang, “Process of the Enantioselective Synthesis of Hydroxypyrrolidines from Amino Acids” U.S. #5,801,247, assigned to Temple University – of the Commonwealth System of Higher Education (1998).
    • E. S. Blake, R. E. DeBrunner, and D. R. Dalton, “Fluorine Containing Phosphoramidates,” U.S. #3,558,748, assigned to the Monsanto Company (1971).
    • E. S. Blake, R. E. DeBrunner, and D. R. Dalton, “Fluorine Containing Organophosphorus Compounds,” U.S. #3,346,647, assigned to the Monsanto Company (1967).
    • E. S. Blake, D. R. Dalton, and R. E. DeBrunner, “Fluorine Containing Organic Compounds of Phosphorus,” U.S. #3,288,890, assigned to the Monsanto Company (1966).

    OTHER REFEREED WORKS PUBLISHED OR IN PRESS:

    • Alkaloids:, Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition, Wiley,, New York, 1991. Vol. 1, pp 1039-1087.
    • “Halogen Hydride Addition to Alkenes and Alkynes”, Trends in Organic Chemistry, 1993, 4, 303-333. Council of Scientific Research Integration, ed. Trivandrum, INDIA
    • “Copper(I) iodide-Potassium naphthalenide”, Encyclopedia of Reagents for Organic Synthesis, Wiley, New York, 1995, 2, 1350.
    • “Copper(I) iodide-tributylphosphine”, Encyclopedia of Reagents for Organic Synthesis, Wiley , New York, 1995, 2, 1351.
    • “Copper(I) iodide-tributylphosphite”, Encyclopedia of Reagents for Organic Synthesis, Wiley , New York, 1995, 2, 1353.
    • “Copper(I) iodide-triethylphosphite”, Encyclopedia of Reagents for Organic Synthesis, Wiley, New York, 1995, 2, 1354.
    • “Copper(I) iodide-trimethylphosphite”, Encyclopedia of Reagents for Organic Synthesis, Wiley, New York, 1995, 2, 1355.
    • “Copper(I) iodide-triethylphosphine-Lithium naphthalenide”, Encyclopedia of Reagents for Organic Synthesis,Wiley , New York, 1995, 2, 1354.
    • Alkaloids:, Kirk-Othmer Condensed Encyclopedia of Chemical Technology, 4th Ed. Wiley, New York, 1999
    • Report: “Strychnine Alkaloids” Encyclopedia of Science and Technology, Ninth Edition, Vol 17. McGraw-Hill Book Co., New York, 2003.
    • Alkaloids:, Kirk-Othmer Encyclopedia of Chemical Technology, On-line Edition, Wiley,, New York, 2003.
    • Alkaloids :, Kirk-Othmer Encyclopedia of Chemical Technology, 5th Edition, Wiley,, New York, 2004. Vol. 2, pp 71-113.
    • Alkaloids Mascavage, L. M.; Jasmin, S. ; Sonnet, P. E.; Wilson, M.; Dalton, D. R. “Alkaloids” in Ullmann’s Encyclopedia of Industrial Technology, Wiley, , DOI:10.1002/14356007.a01_353.pub2, 2011.
    • Book Review: “The Molecules of Nature” by J. B. Hendrickson, Rec. Chem. Progress 1966, 27, 199.
    • Report: “Gas Phase NMR Spectra” TAMU Newsletter 1981, 278-11.
    • Book Review: “The Alkaloids” by M. F. Grundon, J. Am. Chem. Soc. 1983, 105, 5717.
    • Computer Software Review: “Molecular Graphics” by B. H. Robinson, J. Am. Chem. Soc. 1987, 109, 2862.

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