Untersuchungen an diazoverbindungen und aziden-LIII

Theis, Wolfgang; Bethäuser, Willi; Regitz, Manfred

doi:10.1016/s0040-4020(01)96561-5

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1985

1996

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“…3-20 a-Acyldiazoalkanes were reported to yield triazole oligomers (4) rather than monomeric bicyclic diaziridines (3).' 3-16, 19 The assignment of the oligomeric structure (4) was based on molecular weight data obtained by vapour-phase osmometry and ebullioscopic methods. The product from (la) and (Za), for example, was determined to be a trimer of type (4) (R' = C02Et, R2 = H, R3 = Ph).…”

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confidence: 99%

Reaction of diazoalkanes with 4-substituted 1,2,4-triazole-3,5(4H)-diones

Izydore¹,

Chapman²,

Mitchell³

et al. 1988

J. Chem. Soc., Perkin Trans. 2

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Diazoacetic esters reacted with 4-substituted 1,2,4-triazole-3,5(4H) -diones (2) to give one-to-one adducts. Molecular weight determination, high-performance liquid chromatography, and 2D n.m.r. spectroscopy showed that the adducts are monomers that associate in solution. The monomers are most likely 1,3,5-triazabicyclo[3.1 .O] hexane-2,4-diones. The adducts were thermally isomerized to 3,6disubstituted 1,3,5-triazine-2,4( 1 H,3H) -diones. Diphenyldiazomethane reacted with (2) to yield an azomethine imine, which underwent thermal dimerization followed by rearrangement.

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confidence: 99%