Optimization of the Synthesis of n-Phthalimidoalkylthiols as Precursors for w-Aminoalkylthiols as Prepared by Undergraduate Chemistry Students

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 20 (2015) pp 138-143

Optimization of the Synthesis of n-Phthalimidoalkylthiols as Precursors for w-Aminoalkylthiols as Prepared by Undergraduate Chemistry Students

Nabyl Merbouh,* Amir Bahman Samsam Bakhtiari, Dennis Hsiao, Byron D. Gates*

Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC V5A 1S6, Canada, nmerbouh@sfu.ca, bgates@sfu.ca
Received March 10, 2015. Accepted April 20, 2015.

Published: 26 May 2015

Abstract. The synthesis of n-phthalimidoalkylthiols from phthalimide and n,m-dibromoalkane was demonstrated as a general approach to short and medium chain (´ = 1 to 12) functional alkylthiols in an undergraduate laboratory setting. The reaction conditions were demonstrated to be mild enough to directly synthesize n-phthalimidoalkylthiols with a carbon chain containing either double or triple bonds. The syntheses of each of these alkylthiols can be completed in less than 24 h (over a few laboratory periods) with at least a 50% overall yield. Reactivity of n,m-dibromoalkane with phthalimide was monitored with ¹H-NMR to determine the length of time needed for the reaction to reach completion avoiding the inaccurate use of thin layer chromatography. Based on this result, reaction times were reduced by two-thirds from those previously reported in the literature, which was necessary to prepare a method that will accommodate the duration of second year introductory organic or organic spectroscopy courses.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: nmerbouh@sfu.ca, bgates@sfu.ca )

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