Bismuth(III)-Mediated Allylation of Benzaldehyde Dimethyl Acetal: Analysis of First-Order Coupling in the NMR Spectrum

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 10 Issue 2 (2005) pp 133-135

Bismuth(III)-Mediated Allylation of Benzaldehyde Dimethyl Acetal: Analysis of First-Order Coupling in the NMR Spectrum

R. David Crouch*, Anna C. Kreshock, Michael S. Holden

Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896, crouch@dickinson.edu
Received October 4, 2005. Accepted February 4, 2005.

Published online: 26 February 2005

Abstract. We describe our version of a bismuth (III)-mediated allylation reaction of benzaldehyde dimethyl acetal with allyltrimethylsilane. The vinylic hydrogens of the resulting ether can be identified in the ¹H NMR spectrum through a partial analysis of the NMR splitting patterns.

Key Words: Laboratories and Demonstrations; organic chemistry; organic synthesis; NMR spectrometry

(*) Corresponding author. (E-mail: crouch@dickinson.edu)

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Supporting Materials:

Written material for students including a laboratory handout and safety instructions; instructor notes; CAS registry numbers for the reagents; and spectra are available in a Zip file as supporting material (228 KB).