Abstract:The reaction of n-butyl or s-butyl bromide with potassium cyanate in dimethylformamide was carried out at 100°C for 3 hr. to give tri-n-butyl or tri-s-butyl isocyanurate. In this process, the presence of unpolymerized n-butyl or s-butyl isocyanate in the reaction mixture was detected by treating the mixture with benzylamine, thus forming 1-n-butyl or 1-s-butyl-3-benzyl urea. The presence of 1-butanol in the reaction system resulted in an increase in the yield of the corresponding isocyanurates. This tendency w… Show more
“…Dithioamide 8 was also examined to compare the functional group specificity. The known benzylic compounds 9 , 10 , and 11 were prepared as the reference compounds. 1 Synthesis of m -Xylylene Type Dithioureas Possessing a tert -Butyl Group on the Benzene Ring a a Reagents and conditions: (a) (i) potassium phthalimide, DMF, 90 °C, (ii) H 2 NNH 2 ·H 2 O, EtOH, reflux, 57%; (b) RNCS, THF, reflux, 68−94%; (c) 1,1‘-thiocarbonyldiimidazole, THF, room temperature, 32%; (d) RNH 2 , THF, reflux, 74−94%. …”
Dithiourea 1a self-assembles to form an orthogonal dimer structure both in solution and in the solid state, wherein the four thiourea groups establish a closed network of hydrogen bonds through a head-to-tail binding mode. This novel dimer structure was elucidated on the basis of (1)H NMR spectra, vapor pressure osmometry, and X-ray crystal structure analysis. Furthermore, a series of m-xylylene type dithioureas were synthesized and their dimerization constants (K(a)) in CDCl(3) were determined by dilution experiments using (1)H NMR spectroscopy. The magnitude of the K(a) values are dependent on the steric bulk of the side chains, the acidity of the thiourea groups, and the weak intermolecular interaction between the benzene rings of the side chains and the m-xylylene spacer.
“…Dithioamide 8 was also examined to compare the functional group specificity. The known benzylic compounds 9 , 10 , and 11 were prepared as the reference compounds. 1 Synthesis of m -Xylylene Type Dithioureas Possessing a tert -Butyl Group on the Benzene Ring a a Reagents and conditions: (a) (i) potassium phthalimide, DMF, 90 °C, (ii) H 2 NNH 2 ·H 2 O, EtOH, reflux, 57%; (b) RNCS, THF, reflux, 68−94%; (c) 1,1‘-thiocarbonyldiimidazole, THF, room temperature, 32%; (d) RNH 2 , THF, reflux, 74−94%. …”
Dithiourea 1a self-assembles to form an orthogonal dimer structure both in solution and in the solid state, wherein the four thiourea groups establish a closed network of hydrogen bonds through a head-to-tail binding mode. This novel dimer structure was elucidated on the basis of (1)H NMR spectra, vapor pressure osmometry, and X-ray crystal structure analysis. Furthermore, a series of m-xylylene type dithioureas were synthesized and their dimerization constants (K(a)) in CDCl(3) were determined by dilution experiments using (1)H NMR spectroscopy. The magnitude of the K(a) values are dependent on the steric bulk of the side chains, the acidity of the thiourea groups, and the weak intermolecular interaction between the benzene rings of the side chains and the m-xylylene spacer.
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