Kinetics of the formation of benzoguanamine from dicyandiamide and benzonitrile

Ogata, Yoshiro; Kawasaki, Atsushi; Nakagawa, Kurea

doi:10.1016/s0040-4020(01)98493-5

Cited by 13 publications

(5 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The compound 6 is also consistent with IR spectrum. This is in agreement with the mechanism of the guanamine cycloaddition reaction proposed [37]. FIB MS shows molecular peak at 647 (M+I) in a positive ion spectrum.…”

Section: Resultssupporting

confidence: 90%

Guanamine Dendrimerization

Maciejewski

Bednarek²,

Janiszewska

et al. 2000

Journal of Macromolecular Science, Part A

View full text Add to dashboard Cite

A synthesis of dendrimers and hyperbranched polymers by using cycloaddition of cyanoguanidine to nitriles and cyanoethylation reaction is reported. Both reactions proceeded in the presence of a basic catalyst (alkaline hydroxides and Triton B, respectively). ORDER REPRINTSThe guanamine dendrimerization process has been carried out up to 4 th generations ended with cyano or amine groups. Intermediates and product substances, as well as by-products were identified by FT-IR, 1 H and 13 C NMR, MS, FIB-MS, and elemental analysis. Hyperbranched polymers were characterized by gel permeation choursomatography (GPC). Polyguanamine dendrimer (PGD) molecules exhibited expanded form in dimethylacetamide solution and low polydispersity (1.12-1.26). Observed contraction of the macromolecules was growing towards higher generations reaching an extreme at generation 4. The degree of branching of the products were within the range of 0.81-0.87 on the 0-1 scale.Decyanoethylation, hydrolysis, and intramolecular cyclization, as side reactions, were observed on the cycloaddition steps of dendrimerization. Some main stream dendrimerization products, i.e., tetrakis [2-(2,4-diamino-1,3,5-triazin-4-yl)ethyl]2,4-diamino-6-phenyl-1,3,5-triazine and 2,2,6,6-tetrakis[2-(2,4-diamino-1,3,5-triazin-6-yl)ethyl]cyclohexanone as well as by-products, i.e., 2,6,6-tris[2-(2,4-diamino-1,3,5-triazin-6-yl)ethyl] cyclohexanone, 2,6,6-tris(2-cyanoethyl)cyclohexanone and a dilactam have been isolated as new compounds. Spectral data for N 2 N 2 N 4 N 4 -tetrakis(2-cyanoethyl)-6-phenyl-1,3,5-triazine, 2,2,-6,6-tetrakis(2-cyanoethyl)cyclohexanone, 1,1,1-tris(2-cyanoethyl)propanone-2 and 1,1,1-tris[2-(2,4-diamino-1,3,5-triazin-6yl)ethyl]propanone-2 have been complemented. 754 MACIEJEWSKI ET AL.

show abstract

Section: Resultssupporting

confidence: 90%

Guanamine Dendrimerization

Maciejewski

Bednarek²,

Janiszewska

et al. 2000

Journal of Macromolecular Science, Part A

View full text Add to dashboard Cite

show abstract

“…The proposed pathway for the conversion of Ph 3 GeCH 2 CN to 4 and the subsequent transformation of 4 to 5 is shown in Scheme 3, which is consistent with the pathway that has been described for the free amines and related species [20,21]. The transformation of Ph 3 GeCH 2 CN to 4 involves an initial deprotonation at the a-carbon of Ph 3 GeCH 2 CN, and the resulting nucleophilic site attacks the cyano carbon of CH 3 CN and after rearrangement the triphenylgermyl group migrates such that it becomes attached to the nitrogen atom that results from the incoming molecule of CH 3 CN.…”

Section: Tablesupporting

confidence: 82%

“…The NeCa bond in the free amine measures 1.346(1) Å and the NeCaeCb bond Table 1 Bond distances (Å) and angles ( ) for Ph 3 Ge[NHC(CH 3 )CHCN] (4). (7) 111.67(7) Ge(1)eC (7) 1.941(2) C(1)eGe(1)eC (13) 110.75(7) Ge(1)eC (13) 1.939(2) C(7)eGe(1)eC (13) 111.01 (7) Ge (1) (21) 121.6(2) C(20)eC(21)eN (2) 178. 3(2) C(20)eC(19)eC (22) 121.4 (2) angle is 121.6(1) .…”

Section: Resultsmentioning

confidence: 99%

Reactivity of α-germyl nitriles with acetonitrile: Synthesis, structures, and generation of Ph3Ge[NHC(CH3)CHCN] and 2,6-dimethyl-4-(triphenylgermylamino)pyrimidine from Ph3GeCH2CN

Samanamú

Rheingold

Weinert

2011

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

“…Derivatives of s-triazine are also reported to be synthesized from amidines (32) by reacting with phosgene gas, 25 with tertiary amines via copper catalysis, 26 with primary amines under metal-free conditions, 26 with alcohols under highly chemo-selective, base-free conditions via aerobic oxidation, [27][28][29][30] and with diones. 31 Similarly, ethyl acetimidate hydrochloride (33) is reacted with two equivalent monosodium cyanamide (NaNHCN), which on further treatment with hydroxylamine hydrochloride yields derivatives of s-triazine. 32 Likewise, cycloaddition reactions of DICY (34) with aryl and aliphatic nitriles to yield substituted striazines are also reported.…”

Section: Summary Of Synthetic Strategies For S-triazine Derivativesmentioning

confidence: 99%

“…32 Likewise, cycloaddition reactions of DICY (34) with aryl and aliphatic nitriles to yield substituted striazines are also reported. 33 Cyclization of nitriles (35) under Lewis-acid-catalysis yields substituted symmetrical triazines. 34 One-pot synthesis of 1,3,5-triazine can also be carried out via a trimerization reaction of nitriles.…”

Section: Summary Of Synthetic Strategies For S-triazine Derivativesmentioning

confidence: 99%