Diaziridines, 3H‐Diazirines, Diaziridinones, and Diaziridinimines

Heine, Harold W.

doi:10.1002/9780470187197.ch4

Cited by 25 publications

(8 citation statements)

References 187 publications

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“…Other small organic heterocycles in this class include diaziridines 1 and dioxiranes, 2 which have been developed as reagents for a variety of oxidative transformations. η 2 -Peroxo and η 2 -hydroperoxy complexes of various transition metals are also members of this class, 3 and these structures are the active oxidizing species in a broad range of synthetically useful oxidative transformations, including the Sharpless asymmetric epoxidation, 4 VO(acac) 2 -catalyzed epoxidations, 5 and MeReO 3 -catalyzed hydroxylation of unactivated alkanes.…”

Section: Introductionmentioning

confidence: 99%

Advances in the Chemistry of Oxaziridines

2014

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Section: Introductionmentioning

confidence: 99%

Advances in the Chemistry of Oxaziridines

2014

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“…[12][13][14][15] Furthermore, diaziridines are prone to ring expansion reactions with electrophilic reagents (ketenes, isocyanates, isothiocyanates, and acylating reagents), which led to the development of new simple methods for the preparation of both known and previously unknown heterocyclic systems. 8,[16][17][18][19][20] And, finally, diaziridines have a high formation enthalpy as a result of the input both of the hydrazine fragment and three-member strained cycle and of low toxicity, which can be potentially useful for replacing hydrazine derivatives in rocket propellants. However some diaziridines had been absolutely or almost inaccessible (e.g.…”

Section: Introductionmentioning

confidence: 99%

“…[4][5][6] Since that time several reviews on the synthesis and chemical properties of diaziridines have been published. [4][5][6][7][8][9] Diaziridines proved to be unique chemical objects. First of all, diaziridines are among a few matters that contain nitrogen atoms which are configuration-stable under trivial conditions (inversion barriers 20-27 kcal/mol), and, consequently, these compounds have been extensively used to investigate stereochemistry of nitrogen.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of monocyclic diaziridines and their fused derivatives

Махова¹,

Petukhova²,

Кузнецов³

2008

Arkivoc

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Diaziridines and their fused analogues have a wide-range potential as a test subjects for theoretical and practical application. This review covers our investigations focused on the development of optimal methods for the synthesis of monocyclic and fused diaziridine derivatives. Several approaches to the preparation of monocyclic diaziridine derivatives were developed: (1) a synthesis of 3,3-di-and 1,3,3-trialkylmono-and α,ω-bis(diaziridin-1-yl)alkanes from ketoxime O-sulfonates and ammonia, and primary aliphatic amines, respectively, as well as of practically previously inaccessible 3-monoalkyldiaziridines from ammonium salts of aldoxime O-sulfonic acids and ammonia (2) a synthesis of diaziridines from carbonyl compounds, primary aliphatic amines, and aminating reagents in water (or a water-MeOH mixture) at controlled pH of the medium, as well as from carbonyl compounds, amines and N-chloroalkylamines in aprotic solvents in the presence of K 2 CO 3, and (3) a synthesis of 1,2,3-trialkyldiaziridines from Nchloroalkylamines without carbonyl compounds in the presence of primary aliphatic amines at high pressure. As regards fused diaziridine derivatives, general and simple methods were developed to prepare four types of these structures: 1,5-diazabicyclo[3.1.0]hexanes, 1,6-diazabicyclo[4.1.0]heptanes, 1,3,5-triazabicyclo[3.1.0] hexanes, including the parent compound and 2,4-nonsubstituted structures, and 1,3,6-triazabicyclo[3.1.0]hexanes, the latter being previously unknown. The diastereomers have been isolated for 3,3′-bi-and 1,1′-alkylenebisdiaziridines. As a whole the investigations performed in our laboratory have resulted in the simple and general methods for preparing any kind of monocyclic and fused diaziridine derivatives that give high opportunities in the study of their chemical and stereochemical properties, and applications.

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“…Diaziridines, being strained three-membered heterocycles, tend to the ring opening reactions with the formation of reactive intermediates [1][2][3][4]. These reactions can be initiated thermally [5], photochemically [6] or by the action of various reagents.…”

Section: Introductionmentioning

confidence: 99%

Ring Transformation of 1,5‐Diazabicyclo[3.1.0]hexanes under the Action of Arylketenes.

et al. 2006

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Pyrazole derivatives R 0180Ring Transformation of 1,5-Diazabicyclo[3.1.0]hexanes under the Action of Arylketenes. -The interaction of diazabicyclohexanes (I) and (IV) with arylketenes derived from acylchlorides (II) and (V) yields the monocyclic arylacetyl pyrazolidines (III) and (VI) instead of the expected bicycles. Taking into account that the absence of substituents at position 6 of (IV) decreases the steric disfavor for ring closure the cyclization to the expected bicyclic product, e.g. (VIII) and (X), may occur by a thermodynamically-controlled process. The cyclization can proceed both by a concerted and by a two-step mechanism. -(SHEVTSOV, A. V.; KUZNETSOV, V. V.; KISLUKHIN, A. A.; PETUKHOVA, V. Y.; STRELENKO, Y. A.; MAKHOVA*, N. N.; LYSSENKO, K. A.; J. Heterocycl. Chem. 43 (2006) 4, 881-888; Zelinsky Inst. Org.

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Diaziridines, 3H‐Diazirines, Diaziridinones, and Diaziridinimines

Cited by 25 publications

References 187 publications

Advances in the Chemistry of Oxaziridines

Advances in the Chemistry of Oxaziridines

Synthesis of monocyclic diaziridines and their fused derivatives

Ring Transformation of 1,5‐Diazabicyclo[3.1.0]hexanes under the Action of Arylketenes.

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