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Latest revision as of 16:47, 16 July 2021 edit undoJJMC89 bot III (talk | contribs)Bots, Administrators3,663,403 editsm Moving Category:Heterocyclic compounds (1 ring) to Category:Heterocyclic compounds with 1 ring per Misplaced Pages:Categories for discussion/Log/2021 June 24#Category:Heterocyclic compounds (1 ring) |
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{{Distinguish|Diazirine}} |
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{{Chembox |
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| verifiedrevid = 414293886 |
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| ImageFile = diaziridine.png |
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| verifiedrevid = 415901904 |
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| ImageSize = 120px |
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| ImageFileL1 = diaziridine.png |
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| ImageSizeL1 = 130px |
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| IUPACName = Diaziridine |
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| ImageAltL1 = Skeletal formula of diaziridine |
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| OtherNames = |
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| ImageFileR1 = Diaziridine-3D-balls.png |
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| Section1 = {{Chembox Identifiers |
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| CASNo = |
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| ImageSizeR1 = 100 |
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| ImageAltR1 = Ball-and-stick model of the diaziridine molecule |
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| PubChem = 5059686 |
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| PIN= Diaziridine |
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| SMILES = C1NN1}} |
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| SystematicName=Diazacyclopropane |
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| Section2 = {{Chembox Properties |
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| OtherNames = Diazirane<br />1,2-Diazacyclopropane |
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| C=1|H=4|N=2 |
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|Section1={{Chembox Identifiers |
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| Appearance = |
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| CASNo = 463-64-9 |
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| MeltingPt = |
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| PubChem = 5059686 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Solubility = }} |
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| ChemSpiderID = 4236879 |
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| SMILES = N1NC1 |
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| Section3 = {{Chembox Hazards |
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| InChI = 1/CH4N2/c1-2-3-1/h2-3H,1H2 |
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| InChIKey = DIXBSCZRIZDQGC-UHFFFAOYAM |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Autoignition = }} |
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| StdInChI = 1S/CH4N2/c1-2-3-1/h2-3H,1H2 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DIXBSCZRIZDQGC-UHFFFAOYSA-N}} |
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|Section2={{Chembox Properties |
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| C=1 | H=4 | N=2 |
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'''Diaziridines''' are ]s containing two ] atoms in a three-membered ring. They can be considered as strained ]s. Due to the ring strain, the nitrogen atoms are configuration stable leading to ]. |
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'''Diaziridines''' are ]s containing two ] atoms in a three-membered ring. They can be considered as strained ]s. Unlike most ] types of structures, the nitrogen atoms of diaziridines are ] stable because the ring strain prevents ]. As a result, there can be various ]ic forms of this structure. |
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They are usually synthesized by a method developed by E. Schmitz: A ] compound is treated with ] or respectively a primary ] ] and an aminating reagent like ] (HOSA) under slightly basic conditions.<ref>Synthesis of monocyclic diaziridines and their fused derivatives; N. N. Makhova, V. Y. Petukhova, V. V. Kuznetsov, ''Arkivoc'', '''2008'''(i), 128-152. </ref> The final step is based on the intramolecular ] of an ]. |
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They are usually synthesized by treating a ] compound with an aminating reagent like ] and either ] or a primary ] ] under slightly basic conditions.<ref name="Makhova2008">Synthesis of monocyclic diaziridines and their fused derivatives; N. N. Makhova, V. Y. Petukhova, V. V. Kuznetsov, ''Arkivoc'', '''2008'''(i), 128-152. </ref> The final step is based on the intramolecular ] of an ]. |
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==Reactions== |
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==Reactions== |
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* Unsubstituted diaziridines are often directly oxidized (I<sub>2</sub>/NEt<sub>3</sub>) to the more stable ]s. |
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* Unsubstituted diaziridines are often directly oxidized (I<sub>2</sub>/NEt<sub>3</sub>) to the more stable ]s. |
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* They can undergo ring expansion reaction with ] reagents like ]s or ]s. |
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* They can undergo ring expansion reaction with ] reagents like ]s or ]s. |
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* Some derivatives are ] active. |
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* Some derivatives have ] activity.<ref name="Makhova2008"/> |
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==References== |
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==References== |
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{{reflist}} |
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