Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2018 Mar 7;8(18):9718-9722.
doi: 10.1039/c8ra00659h. eCollection 2018 Mar 5.

Convenient and efficient synthesis of functionalized unsymmetrical Z-alkenyl disulfanes

M Musiejuk  1 , J Doroszuk  1 , D Witt  1
Affiliations

Convenient and efficient synthesis of functionalized unsymmetrical Z-alkenyl disulfanes

M Musiejuk et al. RSC Adv. .

Abstract

We developed a simple and efficient method for the synthesis of functionalized unsymmetrical Z-alkenyl disulfanes under mild conditions in moderate to good yields. The designed method is based on the reaction of Z-alkenyl thiotosylates with thiols in the presence of base. The developed method allows the preparation of unsymmetrical Z-alkenyl disulfanes bearing additional hydroxy, carboxy, or amino functionalities.

PubMed Disclaimer

Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Preparation of Z-1-octenyl p-toluenethiosulfonate 4.
See this image and copyright information in PMC

References

    1. Steudel R. Chem. Rev. 2002;102:3905. doi: 10.1021/cr010127m. - DOI - PubMed
    1. Cremlyn R. and An J., Introduction to Organosulfur Chemistry, Wiley, New York, 1996
    2. Oae S., Organic Sulfur Chemistry: Structure and Mechanism, CRC Press, Boca Raton FL, 1991
    3. Vrudhula V. M. MacMaster J. F. Zhengong L. Kerr D. E. Senter P. D. Bioorg. Med. Chem. Lett. 2002;12:3591. doi: 10.1016/S0960-894X(02)00784-9. - DOI - PubMed
    4. Mu Y. Nodwell M. Pace J. L. Shaw J. P. Judice J. K. Bioorg. Med. Chem. Lett. 2004;14:735. doi: 10.1016/j.bmcl.2003.11.040. - DOI - PubMed
    1. Shcherbakova I. and Pozharskii A. F., in Comprehensive Organic Functional Group Transformations II, ed. A. R. Katritzky, R. Taylor and Ch. Ramsden, Pergamon, Oxford, 2004, vol. 2, pp. 177–187
    2. Sato R. and Kimura T., in Science of Synthesis, ed. N. Kambe, J. Drabowicz and G. A. Molander, Thieme, Stuttgart-New York, 2007, vol. 39, pp. 573–588
    3. Witt D. Synthesis. 2008:2491. doi: 10.1055/s-2008-1067188. - DOI
    4. Mandal B. Basu B. RSC Adv. 2014;4:13854. doi: 10.1039/C3RA45997G. - DOI
    5. Musiejuk M. Witt D. Org. Prep. Proced. Int. 2015;47:95. doi: 10.1080/00304948.2015.1005981. - DOI
    1. Harpp D. N. Friedlander B. T. Larsen C. Steliou K. Stockton A. J. Org. Chem. 1978;43:3481. doi: 10.1021/jo00412a013. - DOI
    2. Brown C. Evans G. R. Tetrahedron Lett. 1996;37:9101. doi: 10.1016/S0040-4039(96)02096-5. - DOI
    1. Swan J. M. Nature. 1957;180:643. doi: 10.1038/180643a0. - DOI - PubMed
    2. Hiver P. Dicko A. Paquer D. Tetrahedron Lett. 1994;35:9569. doi: 10.1016/0040-4039(94)88513-3. - DOI