Titrimetric and specteal determination of the basicity of certain diaziridines

Gorshkova, G. N.; Kolodkin, F. L.; Dudinskaya, A. A.; Bova, A. E.; Пономаренко, В. А.; Khmel'nitskii, L. I.; Новиков, С. С.

doi:10.1007/bf00906420

Cited by 3 publications

(3 citation statements)

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“…In aprotic environments, the semistable diazirinyl radical is formed that can act as a strong reducing agents towards other molecules or itself (disproportionation) 12 13 14 . In acidic protic mediums, diaziridine can be protonated, explaining how the diazirine is reduced into the gem-diamine which under goes hydrolysis to the ketone 15 40 . Alternatively, aryl-diaziridine can be oxidized to the original diazirine in caustic pH>11 15 .…”

Section: Figurementioning

confidence: 99%

Adhesive curing through low-voltage activation

et al. 2015

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Instant curing adhesives typically fall within three categories, being activated by either light (photocuring), heat (thermocuring) or chemical means. These curing strategies limit applications to specific substrates and can only be activated under certain conditions. Here we present the development of an instant curing adhesive through low-voltage activation. The electrocuring adhesive is synthesized by grafting carbene precursors on polyamidoamine dendrimers and dissolving in aqueous solvents to form viscous gels. The electrocuring adhesives are activated at −2 V versus Ag/AgCl, allowing tunable crosslinking within the dendrimer matrix and on both electrode surfaces. As the applied voltage discontinued, crosslinking immediately terminated. Thus, crosslinking initiation and propagation are observed to be voltage and time dependent, enabling tuning of both material properties and adhesive strength. The electrocuring adhesive has immediate implications in manufacturing and development of implantable bioadhesives.

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Section: Figurementioning

confidence: 99%

Adhesive curing through low-voltage activation

et al. 2015

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“…12 Hence, to study the reac tions of diaziridines 1 with activated nitriles, we chose 1,2 dialkyldiaziridines 1b-d containing different substitu ents at the carbon atom of the ring and used trichloro acetonitrile as the nitrile. In acetonitrile, the reactions of these compounds at 20-50 °C either did not proceed or (in the presence of BF 3 With the aim of searching for the conditions of the insertion of CS 2 into the diaziridine ring, we consulted the literature on the introduction of other dipolarophiles into the diaziridine ring of 1,5 diazabicyclo[3.1.0] hexanes.…”

Section: Methodsmentioning

confidence: 99%

Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 · Et2O

2009

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The present study revealed two new reactions resulting in the diaziridine ring expansion, viz., the insertion of the CS 2 molecule and the CN group of activated nitriles into the C-N bond of the diaziridine fragment of 6 aryl 1,5 diazabicyclo[3.1.0]hexanes. These reactions can be performed only in ionic liquids in the presence of BF 3 •Et 2 O as the catalyst. Based on these reactions, we developed simple one pot methods for the synthesis of 3 aryldihydro 5H pyrazolo[1,2 c][1,3,4]thiadiazole 1 thiones and 1 aryl 6,7 dihydro 1H,5H pyrazolo [1,2 a] [1,2,4]triazoles in high yields. Dipolar intermediates of new reactions, which are direct precursors of the final products, were detected by NMR methods. One of the intermediates was isolated and characterized. The reaction of 6 aryl 1,5 diazabicyclo[3.1.0]hexanes with benzoyl cyanide affords (2 benzoylpyrazolidin 1 yl)(aryl)acetonitriles.

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“…The basicity of diaziridines is rather low (pK a 4.5-5.5). 6 In this connection, the alkylation would be expected to require polar (or dipolar aprotic) solvents and the presence of inorganic bases. On the other hand, diaziridines are cyclic hydrazines.…”

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confidence: 99%