A Convenient Synthesis of 2-Azido and 2-Thiocyanato-2,3-Unsaturated Cyclic Ketones

Authors

MESUT BOZ
ÖMER ZAİM
HİLAL ESEN

DOI

10.3906/kim-0811-12

Abstract

2-Azido and 2-thiocyanato-2,3-unsaturated ketones were synthesized by utilizing functionalization of 5- or 6-membered cycloalkane-1,2-diones, namely diosphenols, with dimethylthiocarbomoyl chloride, which activates the system towards reaction with nucleophiles in acidic conditions. Replacement of the enolic oxygen of the diosphenols with azide and thiocyanate may be achieved by treating their dimethylthiocarbamates with sodium azide or potassium thiocyanate in boiling acetonitrile/acetic acid.

Keywords

Azides, thiocyanates, enols, deoxygenation, 1, 2-cyclic diketones

First Page

59

Last Page

65

Recommended Citation

BOZ, MESUT; ZAİM, ÖMER; and ESEN, HİLAL (2009) "A Convenient Synthesis of 2-Azido and 2-Thiocyanato-2,3-Unsaturated Cyclic Ketones," Turkish Journal of Chemistry: Vol. 33: No. 1, Article 6. https://doi.org/10.3906/kim-0811-12
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss1/6