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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 3 Issue 2 (1998), S1430-4171(98)02192-4

Synthesis of Diels-Alder Adducts of Phencyclone and NMR Studies of Hindered Rotations of Unsubstituted Bridgehead Phenyls: Microscale Experiments in Organic Chemistry

Ronald Callahan, Kevin Bynum, Ron Prip and Robert Rothchild*

Science Department, The City University of New York, John Jay College of Criminal Justice, New York, NY 10019-1128

Published online: 2 April 1998

Abstract. Synthesis of Diels–Alder adducts of phencyclone with diverse dienophiles provides the basis for a major extended module in the second-semester laboratory of an organic chemistry course. With many accessible target compounds, students can have individual novel compounds to prepare. Especially attractive for students, the adducts are highly hindered, resulting in slow rotation about the C-C sp2-sp3 single bond to the unsubstituted bridgehead phenyl groups. Slow-exchange-limit NMR spectra (1H at 300 MHz and 13C at 75 MHz) are obtained at ambient temperatures for these phenyl groups. The highly crystalline products are easily prepared and offer excellent opportunities to integrate modern 1-D and 2-D NMR techniques into this synthesis experiment, while introducing concepts of dynamic NMR spectroscopy. The synthetic reactions are readily carried out at the microscale level.

Key Words:  Laboratories and Demonstrations; Diels –Alder, organic chemistry; laboratory experiment; NMR; spectroscopy

(*) Corresponding author. (E-mail: not available )

Article in PDF format (1.2 MB )

Supporting Materials:

Appendix. Supporting information for the main article (81 KB) 10.1007/s00897980192b

Issue date: April 2, 1998

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