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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 6
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Original Articles

Reactivity of α,α-Dihalogenated Imino Compounds. Part VIII1. Aziridine Formation by Lithium Aluminium Hydride Reduction of N-2-(1,1-Dichloroalkylidene) Cyclohexylamines

Norbert De Kimpe Laboratory of Organic Chemistry, Faculty of Agricultural Sciences State University of Gent, Coupure 533, B-9000, Gent, Belgium
,
Niceas Schamp Laboratory of Organic Chemistry, Faculty of Agricultural Sciences State University of Gent, Coupure 533, B-9000, Gent, Belgium
&
Roland Verhé Laboratory of Organic Chemistry, Faculty of Agricultural Sciences State University of Gent, Coupure 533, B-9000, Gent, Belgium
Pages 403-408 | Received 05 May 1975, Published online: 06 Dec 2006

Citations (27)

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Norbert De Kimpe, Roland Verhé, Laurent De Buyck & Niceas Schamp. (1980) REACTIVITY OF α-HALOGENATED IMINO COMPOUNDS. Organic Preparations and Procedures International 12:1-2, pages 49-180.
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Articles from other publishers (26)

Navjeet Kaur. 2024. Synthesis of Aziridines and Oxaziridines from Imines. Synthesis of Aziridines and Oxaziridines from Imines 197 212 .
Songlin Zheng & Songlin Zhang. (2016) Synthesis of allyl-aziridines from α-halo oxime ethers and allyl zinc bromides. RSC Advances 6:31, pages 26437-26440.
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Tom Boultwood, Dominic P. Affron & James A. Bull. (2015) Studies on the synthesis of α-iodoaziridines and improved conditions for the synthesis of alkyl-α-iodoaziridines using ClMgCHI2. Tetrahedron 71:30, pages 4949-4957.
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Matthias Moens, Norbert De Kimpe & Matthias D’hooghe. (2014) Selective Synthesis of cis - and trans -2-(Methyl/phenyl)-3-(trifluoromethyl)aziridines and Their Regio- and Stereospecific Ring Opening . The Journal of Organic Chemistry 79:12, pages 5558-5568.
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Desheng Li, Ya Li, Zhiqiu Chen, Huaqi Shang, Hongsen Li & Xinfeng Ren. (2014) Stereoselective synthesis of α-(dichloromethyl)-amines, α-(chloromethyl)amines, and α-chloro-aziridines. RSC Advances 4:27, pages 14254.
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Sonja Stanković, Saron Catak, Matthias D’hooghe, Hannelore Goossens, Kourosch Abbaspour Tehrani, Piet Bogaert, Michel Waroquier, Veronique Van Speybroeck & Norbert De Kimpe. (2011) Synthesis of 3-Methoxyazetidines via an Aziridine to Azetidine Rearrangement and Theoretical Rationalization of the Reaction Mechanism. The Journal of Organic Chemistry 76:7, pages 2157-2167.
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Haibo Mei, Lijun Yan, Jianlin Han, Guigen Li & Yi Pan. (2010) One‐Pot Highly Stereoselective Synthesis of Cyano Aziridines via the CuCl‐Catalyzed Aminochlorination of α , β ‐Unsaturated Nitriles and Intramolecular S N 2 Substitution . Chemical Biology & Drug Design 76:5, pages 392-396.
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Sonja Stanković, Matthias D'hooghe & Norbert De Kimpe. (2010) Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride. Organic & Biomolecular Chemistry 8:19, pages 4266.
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Paula Sério Branco, Vivek Prabhakar Raje, Jorge Dourado & Joana Gordo. (2010) Catalyst-free aziridination and unexpected homologation of aziridines from imines. Organic & Biomolecular Chemistry 8:13, pages 2968.
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Filip Colpaert, Sven Mangelinckx, Erika Leemans, Bram Denolf & Norbert De Kimpe. (2010) Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across α-chloro N-sulfinyl ketimines. Organic & Biomolecular Chemistry 8:14, pages 3251.
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Matthias D'hooghe, Karen Mollet, Stijn Dekeukeleire & Norbert De Kimpe. (2010) Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening. Org. Biomol. Chem. 8:3, pages 607-615.
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Xu-Guang Liu, Yin Wei & Min Shi. (2010) Phosphite-mediated annulation: an efficient protocol for the synthesis of multi-substituted cyclopropanes and aziridines. Tetrahedron 66:1, pages 304-313.
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Lal Dhar S. Yadav, Garima & Ritu Kapoor. (2009) The first diastereoselective nitroaziridination of N-tosylaldimines with 1-bromonitroalkanes. Tetrahedron Letters 50:38, pages 5420-5423.
Crossref
José M. Concellón, Humberto Rodríguez-Solla, Pablo L. Bernad & Carmen Simal. (2009) Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and β-Chloroamines. The Journal of Organic Chemistry 74:6, pages 2452-2459.
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José M. Concellón, Humberto Rodríguez-Solla & Carmen Simal. (2008) Addition Reactions of Iodomethyllithium to Imines. A Direct and Efficient Synthesis of Aziridines and Enantiopure Amino Aziridines. Organic Letters 10:20, pages 4457-4460.
Crossref
Renhua Fan & Yang Ye. (2008) Iodobenzene Diacetate/Tetrabutylammonium Iodide‐Induced Aziridination of N ‐Tosylimines with Activated Methylene Compounds under Mild Conditions . Advanced Synthesis & Catalysis 350:10, pages 1526-1530.
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Guido Verniest, Riccardo Surmont, Eva Van Hende, Arvid Deweweire, Frederik Deroose, Jan Willem Thuring & Norbert De Kimpe. (2008) New Entries toward 3,3-Difluoropiperidines. The Journal of Organic Chemistry 73:14, pages 5458-5461.
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Lal Dhar S. Yadav, Ankita Rai, Vijai K. Rai & Chhama Awasthi. (2008) Novel aziridination of α-halo ketones: an efficient nucleophile-induced cyclization of phosphoramidates to functionalized aziridines. Tetrahedron Letters 49:4, pages 687-690.
Crossref
Norbert De Kimpe & Christian Stevens. (1991) A convenient method for the synthesis of β-chloroamines by electrophilic reduction of α-chloroimines. Tetrahedron 47:20-21, pages 3407-3416.
Crossref
Norbert De Kimpe & Luc Moens. (1990) Synthesis of 1,2,3-trisubstituted and 1,2,2,3-tetrasubstituted aziridines from α-chloroketimines. Tetrahedron 46:8, pages 2965-2974.
Crossref
Norbert De Kimpe, Paul Sulmon & Niceas Schamp. (2010) Study of the Influencing Factors on the Reaction of α‐halogenated Ketimines with Cyanide Ion. Bulletin des Sociétés Chimiques Belges 95:7, pages 567-586.
Crossref
Norbert De Kimpe, Roland Verhé, Laurent De Buyck & Niceas Schamp. (2010) On the mechanism of the rearrangement of N‐aryl α,α‐dichloroketimines with lithium aluminium hydride. Bulletin des Sociétés Chimiques Belges 92:3, pages 233-239.
Crossref
James A. Deyrup. 1983. Chemistry of Heterocyclic Compounds. Chemistry of Heterocyclic Compounds 1 214 .
Norbert de Kimpe, Roland Verhé, Laurent de Buyck & Niceas Schamp. (2010) Reaction of secondary N‐1‐(2‐chloroalkylidene)amines with lithium tetrahydridoaluminate: Synthesis and rearrangement of 1,2,2‐trisubstituted aziridines. Recueil des Travaux Chimiques des Pays-Bas 96:9, pages 242-246.
Crossref
N. DE KIMPE, N. SCHAMP & R. VERHE. (2016) ChemInform Abstract: REACTIVITY OF α,α‐DIHALOGENATED IMINO COMPOUNDS. VIII. AZIRIDINE FORMATION BY LITHIUM ALUMINUM HYDRIDE REDUCTION OF N‐2‐(1,1‐DICHLOROALKYLIDENE)CYCLOHEXYLAMINES. Chemischer Informationsdienst 7:13.
Crossref
Norbert De Kimpe, Roland Verhé, Laurent De Buyck, Walter Dejonghe & Niceas Schamp. (2010) Reactivity of N‐1‐(2,2‐dichloroalkylidene) amides. Bulletin des Sociétés Chimiques Belges 85:10, pages 763-779.
Crossref

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