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ERIC Number: EJ951469
Record Type: Journal
Publication Date: 2011-Nov
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Citrus Peel Additives for One-Pot Triazole Formation by Decarboxylation, Nucleophilic Substitution, and Azide-Alkyne Cycloaddition Reactions
Mendes, Desiree E.; Schoffstall, Allen M.
Journal of Chemical Education, v88 n11 p1582-1585 Nov 2011
This undergraduate organic laboratory experiment consists of three different reactions occurring in the same flask: a cycloaddition reaction, preceded by decarboxylation and nucleophilic substitution reactions. The decarboxylation and cycloaddition reactions occur using identical Cu(I) catalyst and conditions. Orange, lemon, and other citrus fruit peels and juices in the presence of CuSO[subscript 4] lead to the Cu(I)-catalyzed decarboxylation of 3-phenyl-2-propynoic acid to give ethynylbenzene. These click chemistry conditions give Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) of 2-azido-1-phenylethanone with ethynylbenzene to afford 1-phenyl-2-(4-phenyl-1"H"-1,2-3-triazol-1-yl)ethanone regioselectively. (Contains 1 table and 1 scheme.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A