- A hydrazine- and phosgene-free synthesis of tetrazinanones, precursors to 1,5-dialkyl-6-oxoverdazyl radicals
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A complementary approach to published synthetic methods for tetrazinanones, precursors to verdazyl radicals, is described herein. This approach uses carbohydrazide, a commercially available reagent, as a common starting material. Unlike previous methods d
- Bancerz, Matthew,Youn, Beom,Dacosta, Matthew V.,Georges, Michael K.
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p. 2415 - 2421
(2012/05/31)
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- 1,3-Dipolar cycloaddition reactions initiated with the 1,5-dimethyl-3- phenyl-6-oxoverdazyl radical
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The 1,5-dimethyl-3-phenyl-6-oxoverdazyl radical reacts at room temperature in the presence of styrene to give a dihydrotetrazinone heterocyclic structure. We surmise that the reaction occurs by a 1,3-dipolar cycloaddition via the intermediacy of an azomet
- Yang, Angela,Kasahara, Takahito,Chen, Eric K. Y.,Hamer, Gordon K.,Georges, Michael K.
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supporting information; experimental part
p. 4571 - 4574
(2009/05/27)
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- New General Synthesis of Tetrahydro-1,2,4,5-tetrazin-3(2H)-one Derivatives and Stable 3,4-Dihydro-3-oxo-1,2,4,5-tetrazin-1(2H)-yl Radical Derivatives
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Reactions of 2-chloroformylhydrazones of aromatic aldehydes or ketones 2 with various hydrazines were converted to monocarbonohydrazone derivatives 3 or 5 and/or tetrahydro-1,2,4,5-tetrazin-3(2H)-one derivatives 6,7.By oxidation with lead dioxide, compounds 6 were transformed into stable 3,4-dihydro-3-oxo-1,2,4,5-tetrazin-1(2H)-yl radical derivatives 8.
- Milcent, Rene,Barbier, Geo,Capelle, Sylvie,Catteau, Jean-Pierre
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p. 319 - 324
(2007/10/02)
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- 2,4-Dialkyl Substituted Carbono- and Thiocarbonohydrazides, Reactions with Carbonyl Compounds
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2,4-Dialkyl substituted carbono- and thiocarbonohydrazides (4) were prepared from alkylhydrazines and phosgene or thiophosgene.Mono carbonyl compounds reacted with 4 (molar ratio 1:1) to yield hexahydro-1,2,4,5-tetrazines (9, 14; exception 13).Aldehydes in excess generally afforded dihydrazones (3); formaldehyde, however, yielded 1,1'-methylenebis(hexahydro-1,2,4,5-tetrazines) (10) as well as the bicyclic compounds 11 and 12.The constitution of 11 was confirmed by X-ray analysis of 11b.Dialdehydes and aliphatic or alicyclic α-diketones reacted with 4 to give double hexahydro-1,2,4,5-tetrazine derivatives (19), aryl substituted α-diketones on the other hand yielded cyclic dihydrazones (15) and/or mono-hexahydro-1,2,4,5-tetrazines (16).
- Neugebauer, Franz Alfred,Fischer, Hans,Siegel, Rolf,Krieger, Claus
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p. 3461 - 3481
(2007/10/02)
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