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Contents Vol 64(8)

Synthesis of Acyclic, Symmetrical 3,3′-Allyl Dithioethers, from the Alkylation of 3-Mercapto-2-mercaptomethylprop-1-ene in the Presence of Sodium Hydride

Cornelis M. Moorhoff A , Wayne D. Cook A D , Fei Chen A , Dat Nghiem A , Carl Braybrook B , San H. Thang A B , Jiazeng Sun A , Timothy F. Scott C and Christopher N. Bowman C
+ Author Affiliations
- Author Affiliations

A Department of Materials Engineering, Monash University, Clayton, Vic. 3800, Australia.

B Materials Science and Engineering, CSIRO, Clayton, Vic. 3168, Australia.

C Department of Chemical and Biological Engineering, University of Colorado, Boulder, CO 80309-0424, USA.

D Corresponding author. Email: wayne.cook@monash.edu

Australian Journal of Chemistry 64(8) 1083-1093 https://doi.org/10.1071/CH11117
Submitted: 22 March 2011  Accepted: 21 July 2011   Published: 19 August 2011

Abstract

A novel method where 3,3′-allyl dithioethers have been prepared from 3-mercapto-2-mercaptomethylprop-1-ene and two mol equivalent of alkyl halide in the presence of two mol equivalent of sodium hydride has been developed. Using this method, bisepoxide, 2,2′-(2-methylenepropane-1,3-diyl)bis(sulfanediyl)bis(methylene)dioxirane (8) has been synthesized from epichlorohydrin, whereas potassium carbonate was unable to deliver this product. These 3,3′-allyl dithioethers can be utilized either as monomers, or with further chemical reactions transformed into more complex monomers, for photoplastic polymer networks.


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