General and Practical Formation of Thiocyanates from Thiols.

Frei, Reto; Courant, Thibaut; Wodrich, Matthew D.; Waser, Jerome (2014). General and Practical Formation of Thiocyanates from Thiols. Chemistry - A European Journal, 21(6), pp. 2662-2668. Wiley-Blackwell - STM 10.1002/chem.201406171

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A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.

Item Type:

Journal Article (Original Article)

Division/Institute:

School of Architecture, Wood and Civil Engineering

Name:

Frei, Reto;
Courant, Thibaut;
Wodrich, Matthew D. and
Waser, Jerome

ISSN:

0947-6539

Publisher:

Wiley-Blackwell - STM

Language:

English

Submitter:

Admin import user

Date Deposited:

17 Dec 2019 11:01

Last Modified:

17 Dec 2019 11:01

Publisher DOI:

10.1002/chem.201406171

ARBOR DOI:

10.24451/arbor.5811

URI:

https://arbor.bfh.ch/id/eprint/5811

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