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ERIC Number: EJ1011387
Record Type: Journal
Publication Date: 2013-Jan
Pages: 5
Abstractor: As Provided
Reference Count: 18
ISSN: ISSN-0021-9584
Synthesis of Di- and Trisubstituted Azulenes Using a Danheiser Annulation as the Key Step: An Advanced Organic Laboratory Experiment
Thomas, Rebecca M.; Shea, Kevin M.
Journal of Chemical Education, v90 n1 p110-114 Jan 2013
This three-week advanced-level organic experiment provides students with an inquiry-based approach focused on learning traditional skills such as primary literature interpretation, reaction design, flash column chromatography, and NMR analysis. Additionally, students address higher-order concepts such as the origin of azulene's blue color, the mechanism of the Danheiser annulation (step 1), identification of an unknown reaction byproduct, and rationalization of a selective electrophilic aromatic substitution reaction (step 2). Students are initially drawn in by the fascinating color of azulene and remain engaged by the intriguing questions that naturally occur during this investigation. (Contains 5 schemes, 1 table, and 5 figures.)
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:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A