Dr. Tom J. Maricich


Dr. Tom J. Maricich



Professor (1975) 
Synthetic Organic and Physical Organic Chemistry 

Teaching: Graduate & undergraduate organic chem 
E-mail: tmaricic@csulb.edu
Phone: 562.985.4930 
Office: PH2-210 

Area of research: "Click" Alkylation Chemistry of Sulfonimidates

Dr. Maricich's research involves syntheses, reactions, mechanisms, and stereochemistry of SNAAPTM alkylations of various nucleophiles by sulfonimidate esters. SNAAPTM [Substitution, Nucleophilic of Acids, Alcohols and Phenols] refers to alkylation of alcohols by N-tert-butyl-O-ethyl-4-nitrobenzenesulfonimidate [1], which produced unrearranged ethyl ethers in high yields at room temperature within twenty minutes, when catalyzed by the tetrafluoroboric acid dimethyl ether complex. No rearrangements were observed in the ether products formed from 2-methyl-1-propanol, 2-butanol, 2-methyl-2-propanol, neopentyl alcohol, 3-buten-2-ol, menthol, 1-phenylethanol or cinnamyl alcohol. Optically active menthol was ethylated with complete retention of configuration.

Maricich Mechanism

This work was published in December 2013 as a full paper in Synthesis 2013; 45(24): 3361-3368. DOI: 10.1055/s-0033-1339921, entitled SNAAP Sulfonimidate Alkylating Agents for Acids, Alcohols and Phenols on the work of five M.S. and thirteen undergraduate students at CSULB. The key reagent [ethyl N-tert-butyl-4-nitrobenzenesulfonimidate] reported in their paper is now available as the .Maricich ethylation reagent. from Aldrich Chemical Company [Catalog # L512311].

Abstract: Stable, crystalline N-tert-butyl-O-ethyl-4-nitrobenzene-sulfonimidate [1] has been prepared in high yield by direct O-ethylation of N-tert-butyl-4-nitro-benzenesulfonamide with iodoethane and silver in methylene chloride. This sulfonimidate directly ethylates various acids to esters. The stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of HBF4 catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations:. The hard sulfonimidate alkylating agent is chemoselective, preferrring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate.

Future studies will include alkylations of biomolecules like estrogen and cyclic-AMP, competition between various nucleophiles, and reactions of chiral sulfonimidates with prochiral phosphoric and phosphonic acids and with hemiacetals.

Maricich Research Mechanism

Dr. Maricich is continuing in his lab as a full-time emeritus faculty doing writing and research with undergraduates and research volunteers. They are studying new sulfonimidate alkylation reactions, especially those with isopropyl as the alkylating group. In addition to the predominant O-alkylation of phenols, some electrophilic aromatic substitution has been observed.


Brief C.V.

University of Washington, Seattle, Washington, B.S., 1961, Chemistry
Yale University, New Haven, Connecticut, M.S., 1963, Ph.D., 1965,Chemistry


Recent Presentations


Research Assistants at CSULB

2002-2006: Andrea Chen (M.S.), Daniel Savino (President.s Scholar), Christine Bradford (President.s Scholar), Gretchen Witowich (President.s Scholar), Alethea Poste (HHMI Scholar), Omonigho Aisagbonhi (HHMI Scholar), Melissa Garza (RISE Fellow), Dustin Wride, Douglas Thai, Sylvia Kim (summer research assistant from Wellesley College), Andrew Roberts (summer research assistant from UC San Diego), Naoki Kodama

2007-2010: Fan-Chun [Renata] Meng [M.S.], Igor Izotov [M.S. candidate], Michael Fimbres [M.S. candidate], Nai-Chia Kuan [Provost Scholar], Jeremy Wood [Provost Scholar], Francisco Rodriguez [Robert B. Henderson Memorial Scholar, Robert D. Rhodes Award], Marilyn Ton, Holly Phung, Sokrith Sea


Chemical Consulting

Consultant to: Cal OSHA, 1998; Lava Louie, Long Beach, CA, 2005; Intelligent Energy, Ltd., Long Beach, CA, 2007.

Expert chemical witness and consultant to various law firms in litigations related to chemical safety, personal injury, environmental pollution, fire, and explosions for both plaintiffs and defendants, 1986-present.



Among other activities, Dr. Maricich has devoted time to teaching chemistry to primary school students!

Dr. Maricich teaching Chemistry to primary school students Dr. Maricich being innovative with the young students