Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH11117
RESEARCH FRONT
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.


References

[1]  W. D. Cook, F. Chen, Q. D. Nghiem, T. F. Scott, C. N. Bowman, S. Chausson, L. Le PLuart, Macromol. Symp. 2010, 291–292, 50.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  T. F. Scott, A. D. Schneider, W. D. Cook, C. N. Bowman, Science 2005, 308, 1615.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltFemsL4%3D&md5=2180bf456eb2a8d59a5376825afcac19CAS |

[3]  W. D. Cook, S. Chausson, F. Chen, L. Le Pluart, C. N. Bowman, T. F. Scott, Polym. Int. 2008, 57, 469.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXis12lsbc%3D&md5=e260b80f2c7108d978f793b325f9babcCAS |

[4]  (a) T. F. Scott, R. B. Draughon, C. N. Bowman, Adv. Mater. 2006, 18, 2128.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XptlygsLo%3D&md5=3e7b05c6024861c9fb4d9d2addd15b77CAS |
      (b) C. J. Kloxin, T. F. Scott, C. N. Bowman, Macromolecules 2009, 42, 2551.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  Salvatore  R. N., Smith  R. A., Nischwitz  A. K., Gavin  T., Tetrahedron Lett. 2005, 46, 8931. 10.1016/J.TETLET.2005.10.062 and references cited therein.

[6]  M. Feroci, A. Inesi, L. Rossi, Synth. Commun. 1999, 29, 2611.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXktVCiur0%3D&md5=d1c8c30b0d9725a25f84d53bc6cdd7b2CAS |

[7]  H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 2006, 47, 93.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1OisbrL&md5=c5ba65f2f2c86907b776a20975048fb7CAS |

[8]  F. M. Moghaddam, S. M. D. Taimoory, H. Ismaili, G. R. Bardajee, Synth. Commun. 2006, 36, 3599.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmslSisA%3D%3D&md5=f6d0975e290d61daf9fa75053d891d20CAS |

[9]  M. S. R. Murty, R. V. Rao, K. R. Ram, N. R. Reddy, J. S. Yadav, B. Sridhar, Synth. Commun. 2010, 40, 2914.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtVOns7%2FN&md5=b5ad93e1ca7bf98eb825d4856656f99eCAS |

[10]  K. A. Eliazyan, L. V. Shahbazyan, V. A. Pivazyan, E. A. Gharzaryan, A. P. Yengoyan, Heteroatom Chem. 2009, 20, 405.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht12msbg%3D&md5=7b27a47833900ed330d9f5f72bb6eb01CAS |

[11]  L. M. Campos, K. L. Killops, R. Sakai, J. M. J. Paulusse, D. Damiron, E. Drockenmuller, B. W. Messmore, C. J. Hawker, Macromolecules 2008, 41, 7063.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Sjtr3E&md5=9bf51d2cc3841a82fc8a82696c46eaa0CAS |

[12]  X. Zhang, W. Rao, P. W. H. Chan, Synlett 2008, 2204.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) B. A. Trofimov, A. S. Atavin, A. V. Gusarov, S. V. Amosova, S. E. Korostova, Zhurnal Organicheskoi Khimii 1969, 5, 816.
         | 1:CAS:528:DyaF1MXktlyht7w%3D&md5=0ccf36745f6c79e9b0eecb9c38b7223eCAS |
      (b) B. A. Trofimov, A. S. Atavin, A. V. Gusarov, M. F. Shostakovskii, N. I. Golovanova, Izvestiya Akademii Nauk SSSR. Seriya Khimicheskaya 1967, 7, 1591.

[14]  (a) C. Goux, P. Lhoste, D. Sinou, Tetrahedron Lett. 1992, 33, 8099.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXhvFWnurY%3D&md5=ec33fa5796588ce3894ec2bb49ba2366CAS |
      (b) C. Goux, P. Lhoste, D. Sinou, Tetrahedron 1994, 50, 10321.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  (a) R. E. Evans, E. Rizzardo, Macromolecules 2000, 33, 6722.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlslWktbY%3D&md5=809400341181e51753820fc73b98bbafCAS |
      (b) R. E. Evans, E. Rizzardo, J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 202.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  R. W. Alder, Chem. Rev. 1989, 89, 1215.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXksFKltr4%3D&md5=459650897d1cc2a2b0471809ac03cf29CAS |

[17]  A. Sunder, R. Mülhaupt, Macromol. Chem. Phys. 1999, 200, 58.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmtFensg%3D%3D&md5=d8b176b19a237c0fbfabbdcd0088838aCAS |

[18]  J. Emert, R. D. Lundberg, US Patent 5 057 617, 1991.

[19]  X.-J. Liu, R.-Y. Chen, D.-L. Bai, Phosphorus. Sulfur and Silicon 2005, 180, 2607.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1Smt7fF&md5=56836f8ad05eb786921b084b5fbdfcafCAS |

[20]  H. T. Stock, R. M. Kellogg, J. Org. Chem. 1996, 61, 3093.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xit1Khsbs%3D&md5=6ace1f8a8f5a89233442a5b848091c0eCAS |

[21]  X.-P. Gu, I. Ikeda, M. Okahara, Synthesis 1985, 649.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XhsVyht7Y%3D&md5=276568da1481ea673b0e05266eb7ca68CAS |

[22]  (a) D. J. Martin, C. C. Greco, J. Org. Chem. 1968, 33, 1275.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXos1ChtA%3D%3D&md5=ee79154dedf0f907a58ceca4daa6df3dCAS |
      (b) H. Lang, C. Duschl, H. Vogel, Langmuir 1994, 10, 197.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  N. V. Russavskaya, N. A. Korchevin, O. V. Alekminskaya, E. N. Sukhomazova, E. P. Levanova, E. N. Deryagina, Russ. J. Org. Chem. 2002, 38, 1445.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhsFKgtro%3D&md5=2beb28e0f5369561eaf53f2622531c52CAS |