4868-43-3Relevant academic research and scientific papers
A selective synthesis of β-isothiocyanato ketones through a Staudinger/aza-Wittig reaction of β-azido ketones
Fesenko, Anastasia A.,Dem'Yachenko, Ekaterina A.,Fedorova, Galina A.,Shutalev, Anatoly D.
, p. 351 - 359 (2013)
A novel selective two-step synthesis of β-isothiocyanato ketones from α,β-unsaturated ketones has been developed. The synthesis includes preparation of β-azido ketones followed by reaction with triphenylphosphine and carbon disulfide. Treatment of the obtained β-isothiocyanato ketones with ammonia or methylamine gives corresponding hexahydro-4-hydroxypyrimidine-2- thiones. The latter are also prepared directly from β-azido ketones without isolation of the intermediate β-isothiocyanato ketones.
FORMATION OF ISOMERIC β-ISOTHIOCYANATO AND β-THIOCYANATO CARBONYL COMPOUNDS IN THE REACTION OF THIOCYANIC ACID WITH α,β-UNSATURATED ALDEHYDES AND KETONES
Peretokin, A. V.,Shutalev, A. D.,Chupin, V. V.,Mergenova, A. M.,Ignatova, L. A.,et al.
, p. 912 - 918 (2007/10/02)
The structure of the products from the reaction of α,β-unsaturated aldehydes and ketones with thiocyanic acid was established by IR and 1H and 13C NMR spectroscopy.It was shown that the addition temperature and the structure of the obtained product depend on the structures of the initial compounds.It was established that the reactions of α,β-unsaturated aldehydes and ketones not containing methyl substituents at the Cβ carbon atom lead to the formation of isomeric β-isothiocyanato and β-thiocyanato carbonyl compounds, whereas the β-isothionato derivatives are formed exclusively in the case of t he β-methyl- and β,β-dimethyl substituted α,β-unsaturated aldehydes and ketones.
