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Novel synthesis of symmetrical 3,3′-allyl dithioethers as photoplastic monomer precursors by equal molar rate addition of reactants and solvent controlled oligomerization

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Abstract

An alternative method has been developed whereby novel 3,3′-allyl dithioethers, for monomers used in photoplastic polymers, have been synthesized from a synchronized, rapid addition of a concentrated mixture of 2 mol equiv alkyl halide and 1 mol equiv 3-mercapto-2-mercaptomethyl-1-propene (A) in MeOH in one syringe and an equi-volume two mol equivalent sodium methoxide in MeOH in another syringe. Thus, two-fold excess 3-chloro-2-chloromethyl-1-propene (B) with A gave B-A-B and B-A-B-A-B as the main products but no B-A or B-A-B-A due to the mechanism involved and the low solubility of the longer oligomer in MeOH. When the reaction of 2 × A with B was carried out, the main product was A-B-A-B-A-B-A.

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Acknowledgments

The authors wish to acknowledge the support of ARC DP0877382 in this work and would like to thank Dr. Fei Chen for assisting with the photoplasticity experiments, and Drs. Tara Schiller, Daniel Keddie, and San Thang for reading the manuscript and/or helpful discussions.

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Authors and Affiliations

  1. Department of Materials Engineering, Monash University, Clayton, VIC, 3800, Australia

    Cornelis M. Moorhoff & Wayne D. Cook

  2. Materials Science and Engineering, CSIRO, Clayton, VIC, 3169, Australia

    Carl Braybrook

Authors
  1. Cornelis M. Moorhoff
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  2. Wayne D. Cook
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  3. Carl Braybrook
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Corresponding authors

Correspondence to Cornelis M. Moorhoff or Wayne D. Cook.

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Moorhoff, C.M., Cook, W.D. & Braybrook, C. Novel synthesis of symmetrical 3,3′-allyl dithioethers as photoplastic monomer precursors by equal molar rate addition of reactants and solvent controlled oligomerization. Monatsh Chem 144, 891–902 (2013). https://doi.org/10.1007/s00706-013-0942-6

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  • DOI: https://doi.org/10.1007/s00706-013-0942-6

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