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Iodinane- and Metal-Free Synthesis of N-Cyano Sulfilimines: Novel and Easy Access of NH-Sulfoximines
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Section:Abstract
The synthesis of N-cyanosulfilimines can readily be achieved by reaction of the corresponding sulfides with cyanogen amine in the presence of a base and NBS or I2 as halogenating agents. Oxidation followed by C−N bond cleavage affords synthetically useful NH-free sulfoximines.
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Synthesis of CF3-Substituted Sulfoximines from Sulfonimidoyl Fluorides
Rafal Kowalczyk, Andrew J. F. Edmunds, Roger G. Hall, and Carsten BolmOrganic Letters2011 13 (4), 768-771Synthesis of CF3-Substituted Sulfoximines from Sulfonimidoyl Fluorides
Rafal Kowalczyk, Andrew J. F. Edmunds, Roger G. Hall, and Carsten BolmOrganic Letters2011 13 (4), 768-771N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert−Prakash reagent (TMSCF3) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed ...
Iron(II) Triflate as an Efficient Catalyst for the Imination of Sulfoxides
Olga García Mancheño, Jonathan Dallimore, Andrew Plant and Carsten BolmOrganic Letters2009 11 (11), 2429-2432Iron(II) Triflate as an Efficient Catalyst for the Imination of Sulfoxides
Olga García Mancheño, Jonathan Dallimore, Andrew Plant and Carsten BolmOrganic Letters2009 11 (11), 2429-2432The challenging imination of benzyl-, sterically demanding alkyl-, and heteroaryl-substituted sulfoxides has been studied. Iron(II) triflate was identified as a highly efficient and robust catalyst for sulfur imination reactions. A variety of sulfoxides ...
Synthesis and Insecticidal Activity of N-Substituted (1,3-Thiazole)alkyl Sulfoximine Derivatives
Haibo Yu, Zhenfang Qin, Hong Dai, Xin Zhang, Xue Qin, Tingting Wang and Jianxin FangJournal of Agricultural and Food Chemistry2008 56 (23), 11356-11360Synthesis and Insecticidal Activity of N-Substituted (1,3-Thiazole)alkyl Sulfoximine Derivatives
Haibo Yu, Zhenfang Qin, Hong Dai, Xin Zhang, Xue Qin, Tingting Wang and Jianxin FangJournal of Agricultural and Food Chemistry2008 56 (23), 11356-11360The N-substituted alkyl sulfoximine derivatives are a new chemical family of neonicotinoid insecticides. We have designed and synthesized 10 (1,3-thiazole)alkyl sulfoximine derivatives. All compounds were identified by 1H and 13C nuclear magnetic ...
Stereoselective Rhodium-Catalyzed Imination of Sulfides
Florence Collet, Robert H. Dodd and Philippe DaubanOrganic Letters2008 10 (23), 5473-5476Stereoselective Rhodium-Catalyzed Imination of Sulfides
Florence Collet, Robert H. Dodd and Philippe DaubanOrganic Letters2008 10 (23), 5473-5476The preparation of optically active sulfilimines via the catalytic diastereoselective imination of sulfides using a chiral nitrene is described. Excellent yields up to 97% and good diastereoselectivities up to 96% have been obtained. Oxidation of the ...
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- Published In Issue September 13, 2007
- Received July 13, 2007
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