16597-35-6Relevant articles and documents
Macroheterocycles; XIX. A Convenient Synthesis of N-Alkylated Thioureas
Bogatsky, A. V.,Lukyanenko, N. G.,Kirichenko, T. I.,Limich, V. V.
, p. 136 (1984)
-
Metal-Free C?H Borylation of N-Heteroarenes by Boron Trifluoride
Iashin, Vladimir,Berta, Dénes,Chernichenko, Konstantin,Nieger, Martin,Moslova, Karina,Pápai, Imre,Repo, Timo
supporting information, p. 13873 - 13879 (2020/10/02)
Organoboron compounds are essential reagents in modern C?C coupling reactions. Their synthesis via catalytic C?H borylation by main group elements is emerging as a powerful tool alternative to transition metal based catalysis. Herein, a straightforward metal-free synthesis of aryldifluoroboranes from BF3 and heteroarenes is reported. The reaction is assisted by sterically hindered amines and catalytic amounts of thioureas. According to computational studies the reaction proceeds via frustrated Lewis pair (FLP) mechanism. The obtained aryldifluoroboranes are further stabilized against destructive protodeborylation by converting them to the corresponding air stable tetramethylammonium organotrifluoroborates.
C-H activation with elemental sulfur: Synthesis of cyclic thioureas from formaldehyde aminals and S8
Denk, Michael K.,Gupta, Shilpi,Brownie, John,Tajammul, Sabiha,Lough, Alan J.
, p. 4477 - 4486 (2007/10/03)
The C-H activation of cyclic formaldehyde aminals LCH2 (L = RNCH2CH2CH2-NR and RNCH2CH2-NR, R = Me, Et, iPr, tBu, or Ph) with S8 proceeds at unusually low temperatures (T 2S. The reaction constitutes a new, solvent-free method for the synthesis of thioureas that eliminates the toxic and highly flammable CS2. For R = tBu, the ionic carbenium thiocyanates [LCH]+ SCN- dominate the product spectrum and the respective thioureas are obtained in low yield. The reactivity of the analogous sulfur and oxygen ring systems towards S8 was investigated. 1,3-Dithiolane is cleanly converted into 1,3-dithiolane-2-thione (S8, 14 d, 190°C) and resembles the cyclic formaldehyde aminals in this respect. 1,3-Dioxolane (L = OCH2CH2O) is completely inert towards sulfur even under forceful reaction conditions (190°C, 14 d). The formation of thioureas from aminals was investigated at the CBS-4 and B3LYP/6-31G(d) levels of theory.
MACROHETEROCYCLES. XXII. N,N'-DIALKYLDIAZA(OXA)CYCLOALKANETHIONES, SYNTHESIS AND PROPERTIES
Bogat-skii, A. V.,Luk'yanenko, N. G.,Kirichenko, T. I.,Limich, V. V.,Nazarova, N. Yu.,Karpenko, L. P.
, p. 1379 - 1385 (2007/10/02)
During the alkylation of diaza(oxa)cycloalkanethiones with halogenoalkanes in a two-phase system in the presence of potassium carbonate the corresponding N,N'-dialkylthiuronium salts are formed.Heating of the latter under vacuum leads to the elimination of the halogenoalkanes and the formation of N,N'-dialkyldiaza(oxa)cycloalkanethiones, including new crown compounds.The cationic selectivity of the latter with respect to the ions of alkali and alkaline-earth metals was determined.