David Robert Dalton

Temple University

Curriculum Vitae

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, Dayton, Ohio
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.

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). QD251.3.D35 2011. ISBN 978-0-470-47908-7 (cloth)

RESEARCH ARTICLES PUBLISHED OR IN PRESS:

R.K. Summerbell, A.L. Berlingame, D.R. Dalton, and C.K. Dalton, "The Dimethyl-p-dioxanes and the 2,5-Dibutyl-p-dioxanes," J. Org. Chem. 1962 , 27, 4365.
D.R. Dalton, M.P. Cava, and K.T. Buck, "Hindered Rotation in l-Benzyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines", Tetrahedron Lett. 1965, 2687.
M.P. Cava, C.K. Wilkins, Jr., D.R. Dalton, and K. Bessho, "A New Isoquinuclidine Synthesis. A New Route to dl-Dioscorone", J. Org. Chem. 1965, 30, 3771.
M. Shamma, B.S. Dudock, M.P. Cava, K.V. Rao, D.R. Dalton, D.C. DeJongh, and S.R. Schraeder, "Revised Structures of Hernandezine and Thalsimine. Mass Spectrometry of a Bisbenzylisoquinoline Alkaloid", Chemical Communications 1966, 7.
M.P. Cava and D.R. Dalton, "An Improved Synthesis of dl-Anonaine", J. Org. Chem. 1966, 31, 1281.
D.R. Dalton, J.B. Hendrickson, and D.G. Jones, "An Improved Procedure for the Preparation of Bromohydrins", Chemical Communications 1966, 591.
G. Fraenkel, M.P. Cava, and D.R. Dalton, "Hindered Rotation in l-Benzyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines", J. Am. Chem. Soc. 1967, 89, 329.
D.R. Dalton and D.G. Jones, "Halohydrin Formation in Dimethyl Sulfoxide", Tetrahedron Lett. 1967, 2857.
D.R. Dalton, S.A. Liebman, H. Waldman, and R.S. Sheinson, "ESR Detection of the Diphenylmethyl Radical", Tetrahedron Lett. 1968, 145.
D.R. Dalton, V.P. Dutta, and D.G. Jones, "Bromohydrin Formation in Dimethyl Sulfoxide", J. Am. Chem. Soc. 1968, 90, 5498.
D.R. Dalton and S.A. Liebman, "Electron Spin Resonance Studies On Neutral Hydrocarbon Radicals", J. Am. Chem. Soc. 1969, 91, 1194.
D.R. Dalton and S.A. Liebman, "Thermal and Photolytic Decomposition of Diarylmethylenetriphenylphosphazines and Diaryldiazomethanes",Tetrahedron 1969 25, 3321.
J.B. Hendrickson, R.W. Alder, D.R. Dalton, and D.G. Hey, "Some Approaches to Total Synthesis of Lycorine", J. Org. Chem. 1969, 34, 2667.
D.R. Dalton, K.C. Ramey, H.J. Gisler, Jr., L.J. Lendvay, and A. Abraham, "Hindered Rotation in Substituted 1,2,3,4-Tetrahydro-6,7- dimethyoxyisoquinolines", J. Chem. Soc. 1969, 91, 6367.
B.S. Charleston, C.K. Dalton, S.S. Washburne, D.R. Dalton, and S.R. Schraeder "Chemistry of the Vinyl Cation - The Addition of DC1 to Allene",Tetrahedron Lett. 1969, 5147.
D.R. Dalton, R.C. Smith, Jr., and D.G. Jones, "Bromoformate Formation in Dimethylformamide", Tetrahedron 1970, 26, 575.
D.R. Dalton and S.A. Liebman, "Electron Spin Resonance Studies on Neutral Hydrocarbon Radicals - Substituent and Isotope Effects",Tetrahedron 1970, 26, 3265.
D.R. Dalton and V.P. Dutta, "Bromohydrin Formation in Aqueous Dimethyl Sulphoxide; Electronic and Steric Effects", J. Chem. Soc. (B) 1971, 85.
D.R. Dalton, S.I. Miller, C.K. Dalton, and J.K. Crelling, "The Synthesis of Nitrobenzyl)-4-hydroxy-6,7-methylenedioxy-1,2,3,4- tetrahydroiso-quinoline. Synthesis of 1-Substituted-4-oxygenated-1,2,3,4- tetrahydroisoquinolines", Tetrahedron Lett. 1971, 575.
D.R. Dalton, R.K. Rodebaugh, and C.W. Jefford, "Bromohydrin Formation in Dimethyl Sulfoxide. V. The Reaction of Norbornene", J. Org. Chem. 1972, 37, 363.
D.R. Dalton and R.M. Davis, "Bromohydrin Formation in Dimethyl Sulfoxide. The Reaction of Conjugated Dienes",Tetrahedron Lett. 1972, 1057.
D.R. Dalton and A.A. Abraham, "The Synthesis of Aporphine Alkaloids III. Steric Effects in the Pschorr Cyclization", Synthetic Communications 1972 2, 303.
D.R. Dalton, H.G. Foley, K.N. Trueblood, and M.R. Murphy, "Unusual Nitrones" Tetrahedron Lett. 1973, 779.
S.A. Liebman, D.R. Dalton, T. Knudsen, and G. Underwood, "Stereochemistry of the Diphenylmethyl Radical", J. Mag. Res. 1973, 10, 85.
H.G. Foley and D.R. Dalton, "A Convenient, Neutral Conversion of Aldoximes to Nitriles at Low Temperature", Chemical Communications 1973, 628.
D.R. Dalton and H.G. Foley, "O-Carbamoyl Oximes", J. Org. Chem. 1973, 38, 4200.
H.G. Foley and D.R. Dalton, "A General, Neutral Beckmann Rearrangement of Ketoximes. The Isolation of an Intermediate", Synthetic Communications 1974 4, 251.
F. Amar, D.R. Dalton, G. Eisman, and M.J. Haugh, "The Uncatalyzed Gas Phase Hydrochlorination of Alkenes I. Propene and Isobutylene", Tetrahedron Lett. 1974 3033.
F. Amar, D.R. Dalton, G. Eisman, and M.J. Haugh, "The Uncatalyzed Gas Phase Hydrochlorination of Alkenes II. Allene", Tetrahedron Lett. 1974, 3037.
M.J. Haugh and D.R. Dalton, "The Gas Phase Addition of Hydrogen Chloride to Propylene", J. Am. Chem. Soc. 1975 , 97, 5674.
G. Krow, M. Damodaran, E. Michner, S.I. Miller, and D.R. Dalton, "Nonsymmetric 9-Phenanthrylamines. An Improved Synthetic Procedure to a Useful Synthon", Synthetic Communications 1976, 6, 261.
A.I. Scott, J. Kang, D.R. Dalton, and S.K. Chang, "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.
A.W. Langman and D.R. Dalton, "Bromohydrins from Alkenes and N-Bromosuccinimide in Dimethyl Sulfoxide: erythro-2-Bromo-1,2-Diphenylethanol", Organic Synthesis Wiley,, New York, 1979, 59, 16.
S.S. Washburne and D.R. Dalton, "An Analogy for Quantization of Energy Levels." J. Chem. Educ. 1980, 57, 200.
S. Chackalamannil and D.R. Dalton, "The Synthesis of erythro and threo-N-methyl 7- Hydroxy-1,2,9,10-tetramethoxyaporphine", Tetrahedron Lett. 1980, 2029.
J. Tierney and D.R. Dalton, "A Homemade High Pressure Gas Cell", J. Chem. Ed. 1981, 58, 813.
K.L. Wert, S. Chackalamannil, E. Miller, D.R. Dalton, D.E. Zacharias, and J. P. Glusker, "Hoffmann Degradation of á-Hydroxy Ammonium Salts. alpha- and beta-Hydroxylaudanosine, 7-Hydroxyglaucine, and 13-Hydroxyxylopinine", J. Org. Chem. 1982, 47, 5141.
F. Costello, D.R. Dalton, and J.A. Poole, "Hydrochlorination of Alkenes. 2. Reactions of the Gases Hydrogen Chloride and 2-Methylpropene", J. Phys. Chem. 1986, 90, 5352.
J. Tierney, F. Costello, and D.R. Dalton, "Hydrochlorination of Alkenes. 3. Reactions of the Gases Hydrogen Chloride and E- and Z-2-Butene", J. Org. Chem. 1986, 51, 5191.
H. Doshi, A.B. Cardis, J.K. Crelling, S.I. Miller, D.R. Dalton, D.E. Zacharias, J.P. Glusker, "Hoffman Degradation of á-Hydroxy Ammonium Salts. II. 4-Hydroxybenzylisoquinolines and 4-Hydroxyaporphines", J. Org. Chem. 1987, 52, 2604.
D. M. Schnur and D. R. Dalton, "MM2 Force Field Parameters for Oximes", J. Org. Chem. 1988, 53, 3313.
D. M. Schnur, Y. H. Yuh, and D. R. Dalton, "A Molecular Mechanics Study of Amide Conformations," J. Org. Chem. 1989, 54, 3779.
J. Eshraghi, J. Longo, D. R. Dalton and G. W. Harrington, "An Unusual Ring Contraction in the Formation of N-Nitrosohexamethyleneimine and N- Nitrosopiperidine from Tolazamide", Japanese J. Cancer Res. (Gann) 1990, 81, 324.
L. M. Mascavage, H. Chi, S. La and D. R. Dalton, "Surface-Catalyzed Hydrochlorination of Alkenes. The Reaction of the Gases Hydrogen Chloride and 1,3-Butadiene", J. Org. Chem. 1991, 56, 595.
L. M. Mascavage and D. R. Dalton, "Surface Catalyzed Hydrochlorination of 1,3-Butadiene", Tetrahedron Lett. 1991, 32, 3461.
B.-C. Kao, H. Doshi, H. Reyes-Rivera, D. D. Titus, M. Yin, and D. R. Dalton, 3-Substituted 2-Pyridinecarbaldoximes", J. Heterocyclic Chem. 1991, 28, 1315.
A. D. Grant, D. E. Zacharias, L. M. Mascavage, G. E. Kemmerer, and D. R. Dalton "Chloromethylation of Codeine. Isolation of a Quaternary Iodide", J. Heterocyclic Chem. 1993, 30, 553.
S. Jasmin, D. R. Dalton, P. J. Carroll and B.-C. Kao, "The Synthesis and Spontaneous Resolution of 2-(3-Thioxothiazolidin-3-yl)thiazole." J. Heterocyclic Chem. 1994 31, 1079.
L. M. Mascavage, F. Zhang and D. R. Dalton, "The Reaction of the Gases Hydrogen Chloride and 2-Butyne." J. Org. Chem. 1994, 59, 5048.
H. M. Reyes-Rivera, R. O. Hutchins and D. R. Dalton, "2-Carbaldoximes of Pyridine 4- and 5-Carboxylic Acids." J. Heterocyclic Chem. 1995, 32, 665.
Y. Huang, D. R. Dalton and P. J. Carroll, "The Efficient, Enantio- selective Synthesis of Aza Sugars from Amino Acids. 1. The polyhydroxylated Pyrrolidines". J. Org. Chem. 1997,62, 371.
Y. Huang, P. E. Sonnet, P. J. Carroll, and D. R. Dalton, "Diastereoselective Diels-Alder Reactions. The Role of the Catalyst.",Tetrahedron Lett. 2000 , 41, 2519.
L. M. Mascavage, Q. Lu, J. Vey, D. R. Dalton and P. J. Carroll, "Enantioselective Synthesis of Aza Sugars from Amino Acids. 2. The 3-Hydroxy-2-hydroxymethylpyrrolidines." J. Org. Chem. 2001,66, 3621.
Y. Huang, P. E. Sonnet and D. R. Dalton, "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 ,
M. L. Wilson, D. R. Dalton and P. J. Carroll, "Decoration of the Aromatic Ring of Dihydrocodeinone (Hydrocodone) and 14-Hydroxydihydrocodeinone (Oxycodone)". J. Org. Chem. 2005, 70, 6492.
L. M. Mascavage, M. L. Wilson and D. R. Dalton, " Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools." Current Organic Synthesis , Current Organic Synthesis 2006 , 3 99.
L. M. Mascavage, P. E. Sonnet and D. R. Dalton, "On the Surface-Catalyzed Reaction between the Gases 2,2-Dimethylpropanal and Methanamine. Formation of Active-Site Imines." J. Org. Chem. 2006, 71 , 3435.
P.E. Sonnet, L.M. Mascavage and D.R. Dalton, "The First Steps. The Attack on the Carbonyl Carbon of Pyridoxal Cofactor in Pyridoxal- Dependent Enzymes." , Bioorg. Med. Chem. Let. 2008,18, 744.
L.M. Mascavage, F. Zhang-Plasket, P.E. Sonnet and D. R. Dalton, "Gas phase surface-catalyzed HCl addition to vinylacetylene: motion along a catalytic surface. Experiment and theory." Tetrahedron 2008 , 64, 9357.
L. M. Mascavage, J. Tierney, P. E. Sonnet and D. R. Dalton, "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 .
E. J. Judge, J. J. Brady, D. Dalton and R. J. Levis, "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 , 3231-3238.

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.

COURSES TAUGHT IN THE LAST FIVE YEARS:

Undergraduate

Introduction to Chemistry II
General Chemistry for Majors/Honors I and II
General Chemistry for Majors/Honors Laboratory I and II
Organic Chemistry I and II
Organic Chemistry Laboratory
Organic Chemistry for Majors/Honors I and II
Organic Chemistry for Majors/Honors Laboratory I and II
Techniques of Chemical Measurement II
Computer Information Science (Molecular Modeling)

Graduate

Organic Reaction Mechanisms
Organic Synthesis
Organic Chemistry of Biological Pathways (Natural Products)
Heterocycles
Special Topics in Organic Chemistry (Organic Chemistry with Computers)
Special Topics in Organic Chemistry (Tandum Organic Reactions)

NAME SPECIAL AWARDS RECEIVED FOR TEACHING EXCELLENCE:

The Christian R. and Mary F. Lindback Foundation Award for Distinguished Teaching, Temple University, 1975.

The College of Arts and Sciences Alumni Award for Excellence in Teaching, Temple University, 1986.

American Institute of Chemists, Philadelphia Area, Scroll Awardee, May, 1989.

Visiting Master Teacher in Residence, Clemson University, Clemson, S.C., 1994.

The Great Teacher Award, Temple University, 1997.

The Philadelphia Section, American Chemical Society Award (Sponsored by Merck, Inc.) for "Excellence in Teaching Undergraduate Chemical Science," 2003

Honors Professor of the Year, 2005. Voted by the students of the Temple University Honors Program .

MASTER'S THESES SUPERVISED:

1969: B. S. Charleston
1972: R. M. Davis
1981: K. L. Wert
1981: E. Miller
1983: S. Chackalamannil
1989: H. Chi
1990: D. Agostine
1992: W. Pastore
1995: X. Gong
1995: J. Rogers
1996: F. Zhang
1997: Y. Huang
1998: Q. Lu
1999: Y. Wang
2008: M. Beaston
2010: S. Jolly

DOCTORAL DISSERTATIONS SUPERVISED:

1969: V. P. Dutta
1969: S. A. Liebman
1971: S. I. Miller
1971; R. K. Rodebaugh
1972: A. A. Abraham
1974: H. G. Foley
1977: A. B. Cardis
1977: J. K. Crelling
1980: J. Tierney
1984: F. Costello
1985: Y. H. Yuh
1986: M. P. Hinton
1986: H. Doshi
1987: V. A. Hegde
1987: K. A. Stetyick
1988: M. Costanzo
1988: B. Kao
1988: D. Schnur
1994: H. M. Reyes-Rivera
1996: S. Jasmin

CURRENT PROFESSIONAL COLLEAGUES AT TEMPLE UNIVERSITY

Dr. Linda M. Mascavage
Dr. David Hill
Dr. Phil Sonnet
Dr. Mike Wilson

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