- Frustrated Lewis pair activation of an N-sulfinylamine: A source of sulfur monoxide
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Inter- and intramolecular P/B frustrated Lewis pairs are shown to react with an N-sulfinylamine to form PNSOB linakages. These species can be regarded as phosphinimine- borane-stabilized sulfur monoxide complexes, and indeed these species act as sources of SO, effecting the oxidation of PPh3 and delivering SO to [RhCl(PPh3)3] and an N-heterocyclic carbene.
- Longobardi, Lauren E.,Wolter, Vanessa,Stephan, Douglas W.
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- Synthesis of benzo-ortho-thiazines S-oxides by diels-alder reaction of N-sulfinylanilines with norbornadiene
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From substituted N-sulfinylanilines acting as dienes in the Diels-Alder reaction with norbornadiene S-oxides of benzo-ortho-thiazines were obtained, which were oxidized into the corresponding S,S-dioxides belonging to the class of hybrid thiazinesulfonami
- Veremeichik,Merabov,Chuiko,Lodochnikova,Plemenkov
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p. 1605 - 1609
(2014/02/14)
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- Synthesis of six-membered cyclic sulfonimidamides
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A general synthetic route to six-membered cyclic N-aryl- and N-alkyl-substituted sulfonimidamides via an intramolecular ring closure of suitably functionalised acyclic sulfonimidamides is described. The structure of this new ring system was confirmed by v
- Sen, Indira,Kloer, Daniel,Hall, Roger,Pal, Sitaram
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p. 3018 - 3028
(2013/11/06)
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- N-heterocyclic carbene catalysis: Enantioselective formal [2+2] cycloaddition of ketenes and N-sulfinylanilines
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Sultam of swing: Both enantiomers of 1,2-thiazetidin-3-one oxides were obtained in very good yields with excellent enantioselectivities when using N-heterocyclic carbene catalysts (see scheme; M.S.=molecular sieves, TBS=tert-butyldimethylsilyl). The products were easily converted into 3-oxo-β-sultams, α-mercapto amides, and β-mercapto amines through oxidation or reduction. Copyright
- Jian, Teng-Yue,He, Lin,Tang, Cen,Ye, Song
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supporting information; body text
p. 9104 - 9107
(2011/10/13)
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- A-new synthesis of N-sulfinylamines via β-elimination of chloroform from trichloromethanesulfinamides
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The synthesis of various N-monosubstituted trichloromethanesulfinamides by two alternative and novel procedures is described. All these compounds have been found to undergo base-induced elimination of chloroform with formation of the corresponding N-sulfinylamines. Reaction proceeds smoothly under mild conditions.
- Braverman, Samuel,Cherkinsky, Marina
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p. 487 - 490
(2007/10/03)
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- Substituted N-aryl alk-1-enesulfinamides: Preparation, properties and conversion into the corresponding indole compounds [1]
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Reaction of vinylic organometallic derivatives with N-sulfinyl arenamines 2 affords the title sulfinamides 3. On heating their solutions in selected solvents to 80-124 °C, these sulfinamides are converted into the corresponding indoles 6, probably via a [3.3]-sigmatropic rearrangement to intermediates VIII which undergo an intramolecular carbophilic reaction of the nitrogen atom with the neighboring sulfine group, followed by elimination of HSOH. The triethyloxonium tetrafluoroborate- or boron trifluoride etherate catalyzed conversion 3 → 6 can be carried out at a much lower temperature. Elsevier,.
- Baudin, Jean-Bernard,Commenil, Marie-Gabrielle,Julia, Sylvestre A.,Lorne, Robert,Mauclaire, Laurent
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p. 329 - 350
(2007/10/03)
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- 6?-Cycloadditions of Aryl and New Heteroaryl N-Sulphinylamines With 2,3-Dimethylbuta-1,3-diene: Synthesis, Kinetics, Substituent Effects, Theoretical Calculations, and Reaction Mechanism
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A range of new N-sulphinylamine derivatives of heteroaryl rings, including tetrazoles, oxadiazoles, thiadiazoles, thiazoles, and oxazoles is reported.The influence of the -N=S+-O- group on the n.m.r. spectra of the ring to which it i
- Butler, Richard N.,O'Halloran, Gerard A.,Burke, Luke A.
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p. 1855 - 1860
(2007/10/02)
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- NEW FACILE SYNTHESIS OF α-HYDROXYAMIDES:INTERMOLECULAR AND INTRAMOLECULAR CATALYSIS IN THE REACTION OF α-HYDROXYCARBOXYLIC ACIDS WITH N-SULFINYLAMINES.
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α-Hydroxycarboxylic acids (1) reacted with N-sulfinylanilines (2) to give the corresponding α-hydroxyanilides (5) in quantitative yields under mild condition: the reaction appears to involve intermolecular catalysis by the carboxylic acid moiety and intra
- Shin, Jai Moo,Kim, Yong Hae
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p. 1921 - 1924
(2007/10/02)
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- NEW FACILE SYNTHESIS OF N-SULFINYLAMINE DERIVATIVES USING N,N'-SULFINYLBISIMIDAZOLE AND N-(CHLOROSULFINYL)IMIDAZOLE
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Treatment of amine derivatives such as amines, sulfonamides, and amides with N,N'-sulfinylbisimidazole (1) and N-(chlorosulfinyl)imidazole (2) in situ respectively gives the corresponding N-sulfinylamine derivatives (3): the latter reaction using N-(chlor
- Kim, Yong Hae,Shin, Jai Moo
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p. 3821 - 3824
(2007/10/02)
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- 1,2-Thiazines and Related Heterocycles. Part 1. An Investigation of the Cycloadditions of N-Sulphinylanilines with 1,4-Epoxy-1,4-dihydronaphthalene and Other Alkenes
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Evidence is adduced from the character of the alkenes which cycloadd to N-sulphinylanilines and from a kinetic investigation of the reactions of N-sulphinylanilines with 1,4-epoxy-1,4-dihydronaphthalene, examining the effects upon reaction rate of solvent polarity, temperature, and substitution in the N-sulphinylanilines, that the cycloadditions are pericyclic reactions of Diels-Alder type with inverse electron demand.A degree of charge separation in the transition state is indicated but this is small and confined essentially to the sulphinylaniline moiety.
- Hanson, Peter,Lewis, Robin J.,Stone, Thomas W.
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p. 1719 - 1724
(2007/10/02)
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- Heterocyclic Synthesis with Malonyl Dichloride. Part 13. 6-Chloro-4-hydroxy-2-oxypyran-3-carboxanilides from N-Sulphinylanilines and Further Reactions of Malonyl Dichloride with Thiocyanates
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N-Sulphinylanilines react with malonyl dichloride to give 6-chloro-4-hydroxy-2-oxopyran-3-carboxanilides with loss of the sulphoxide moiety as thionyl chloride.Milder conditions and electron-withdrawing substituents do not alter the course of the reaction of thiocyanates with malonyl dichloride to give 2-substituted-thio-7-chloro-4H,5H-pyranooxazine-4,5-diones.
- Al-Ajely, Mohammed S.,Al-Rawi, Jasim M. A.,Elvidge, John A.
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p. 1575 - 1578
(2007/10/02)
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