Dr. Tom J. Maricich
Synthetic Organic and Physical Organic Chemistry
Teaching: Graduate & undergraduate organic chem
Area of research: "Click" Alkylation Chemistry of Sulfonimidates
Our research involves syntheses, reactions, mechanisms, and stereochemistry of .Click. alkylations
of various nucleophiles by chiral sulfonimidate esters. "Click" refers to facile reactions occurring
rapidly under mild conditions, selectively giving high yields of products, which are readily isolated
in pure form. For example, click alkylation of alcohols by
N-t-Butyl-O-ethyl-p-nitrobenzenesulfonimidate 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. Uncatalyzed
esterification of acids [pKa less than 7] were spontaneous and quantitative. Alkylations were also
obtained with cholesterol, phenols, thiols, amides and saccharin.
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.
University of Washington, Seattle, Washington, B.S., 1961, Chemistry
Yale University, New Haven, Connecticut, M.S., 1963, Ph.D., 1965,Chemistry
- The Chemistry of Alkyl Sulfonimidates,. California State University, Long Beach, December, 2004.
- Andrea I. Chen (presenter), Tom J. Maricich, Dustin Wride, Matthew J. Allan, Brett Kislin, and Nguyen-Phuong Pham, .Alkylation Reactions of O-Alkyl Sulfonimidates,. 40th Western Regional Meeting of The American Chemical Society (Anaheim), Paper No. 127, January 2006.
- Outstanding Undergraduate Poster Award at the American Chemical Society Western Regional Meeting 2007 Frontiers in Chemistry, Biopharmaceuticals & Biotechnology in San Diego October 9-13, 2007. We were acknowledged at the meeting and awarded one of five awards [out of sixty posters] for our poster entitled "Facile, One-Step Alkylation of Alcohols and Phenols by N-t-Butyl-O-Ethyl-p-Nitrobenzenesulfonimidate," by Christine Bradford, Nai-Chia Kuan, Jeremy Wood and Tom J. Maricich, California State University, Long Beach, Long Beach, CA [Abstract #443].
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
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!