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ERIC Number: EJ1117364
Record Type: Journal
Publication Date: 2016-Oct
Pages: 4
Abstractor: As Provided
ISSN: ISSN-0021-9584
Saccharin Derivative Synthesis via [1,3] Thermal Sigmatropic Rearrangement: A Multistep Organic Chemistry Experiment for Undergraduate Students
Fonseca, Custódia S. C.
Journal of Chemical Education, v93 n10 p1781-1784 Oct 2016
Saccharin (1,2-benzisothiazole-3-one 1,1-dioxide) is an artificial sweetener used in the food industry. It is a cheap and easily available organic compound that may be used in organic chemistry laboratory classes for the synthesis of related heterocyclic compounds and as a derivatizing agent. In this work, saccharin is used as a starting material in a sequential synthesis designed for completion in three laboratory periods of 4 h each. This synthesis includes two nucleophilic substitutions, namely, the transformation of saccharin into saccharyl chloride and the addition of cinnamyl alcohol to saccharyl chloride (3-chloro-1,2-benzisothiazole 1,1-dioxide) to yield O-cinnamylsaccharin [(E)-3-(3-phenylprop-2-enoxy)-1,2-benzisothiazole 1,1-dioxide]. The third reaction is the isomerization of O-cinnamylsaccharin into N-cinnamylsaccharin [2-(3-phenyl-2(E)-propen-1-yl)]-1,2-benzisothiazole-3(2H)-one 1,1-dioxide], a [1,3] sigmatropic rearrangement. The products are characterized using melting point, IR, and [superscript 1]H NMR spectroscopy. These experiments allow students to acquire experience in a multistep synthesis, practice the most typical laboratory scale synthesis, isolation, purification, and analytical methods, and think through and discuss the mechanisms of the intervening reactions.
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Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Identifiers - Location: Portugal
Grant or Contract Numbers: N/A