Global InformationDiaziridine information
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| Names | |||
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| Preferred IUPAC name
Diaziridine | |||
| Systematic IUPAC name
Diazacyclopropane | |||
| Other names
Diazirane
1,2-Diazacyclopropane | |||
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CAS Number
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| Properties | |||
Chemical formula
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CH4N2 | ||
| Molar mass | 44.057 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Diaziridines are heterocyclic compounds containing two nitrogen atoms in a three-membered ring. They can be considered as strained hydrazines. Unlike most amine types of structures, the nitrogen atoms of diaziridines are configurationally stable because the ring strain prevents Walden inversion. As a result, there can be various stereoisomeric forms of this structure.
They are usually synthesized by treating a carbonyl compound with an aminating reagent like hydroxylamine-O-sulfonic acid and either ammonia or a primary aliphatic amine under slightly basic conditions.[1] The final step is based on the intramolecular cyclization of an aminal.
- ^ Synthesis of monocyclic diaziridines and their fused derivatives; N. N. Makhova, V. Y. Petukhova, V. V. Kuznetsov, Arkivoc, 2008(i), 128-152.[1]