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Updated: Jun 1, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
1-(4-Bromo-phen-yl)-3-(2-thienylcarbon-yl)thio-urea
Abstract:
The title compound, C(12)H(9)BrN(2)OS(2), consists of two planar parts, viz. the thio-phene ring including all substituents (r.m.s. deviation 0.007 Å) and the benzene ring including the respective substituents as well as the thione group (r.m.s. deviation 0.05 Å). The inter-planar angle is 18.84 (6)°. An intra-molecular C(phen-yl)-N-H⋯OC hydrogen bond is observed. The three-dimensional packing involves three types of inter-actions, viz. N-H⋯S, C-H⋯S (× 2) and Br⋯S [3.6924 (6) Å].
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

