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

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Turkish Journal of Chemistry
Volume:33 Issue:1
A Convenient Synthesis of 2-Azido and 2-Thiocyanato-2,3-Unsaturated Cyclic Ketones

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

Authors : Mesut BOZ, Ömer Zaim And Hilal ESEN, Ömer ZAİM, Hilal ESEN

Pages : 59-65

View : 15 | Download : 12

Publication Date : 0000-00-00

Article Type : Research Paper

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

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