- Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
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We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
- Delost, Michael D.,Njardarson, Jon T.
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supporting information
p. 6121 - 6125
(2021/08/16)
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- Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide
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A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.
- Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu
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supporting information
p. 8691 - 8695
(2021/10/22)
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- Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization
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[n.3.0]Bicycles (n = 3-6) can be synthesized using palladium-catalyzed asymmetric allylic alkylation followed by rutheniumcatalyzedcycloisomerization.Newtypesoftriarylphosphino-1,2-diaminooxazolineligandsshowthesamehighlevelsofenantioselectivity observed with Trost ligand when employed in Pd-catalyzed allylic alkylation reactions. The enyne products of these allylic alkylation reactions were further elaborated using a Ru-catalyzed redox isomerization process, for which a mechanism is proposed.
- Havare, Nizam
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p. 1445 - 1462
(2021/01/05)
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- Base-free Enantioselective C(1)-Ammonium Enolate Catalysis Exploiting Aryloxides: A Synthetic and Mechanistic Study
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An isothiourea-catalyzed enantioselective Michael addition of aryl ester pronucleophiles to vinyl bis-sulfones via C(1)-ammonium enolate intermediates has been developed. This operationally simple method allows the base-free functionalization of aryl esters to form α-functionalized products containing two contiguous tertiary stereogenic centres in excellent yield and stereoselectivity (all ≥99:1 er). Key to the success of this methodology is the multifunctional role of the aryloxide, which operates as a leaving group, Br?nsted base, Br?nsted acid and Lewis base within the catalytic cycle. Comprehensive mechanistic studies, including variable time normalization analysis (VTNA) and isotopologue competition experiments, have been carried out. These studies have identified (i) orders of all reactants; (ii) a turnover-limiting Michael addition step, (iii) product inhibition, (iv) the catalyst resting state and (v) catalyst deactivation through protonation.
- McLaughlin, Calum,Slawin, Alexandra M. Z.,Smith, Andrew D.
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supporting information
p. 15111 - 15119
(2019/11/05)
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- Sulfones as Synthetic Linchpins: Transition-Metal-Free sp3–sp2 and sp2–sp2 Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds
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A valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin is reported. Although the bis(phenylsulfonyl)methyl group is typically introduced as an sp3-carbon nucleophile, it is demonstrated that it can also function as an effective sp2-carbon electrophile in the presence of organolithium nucleophiles. Alkyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross-couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at ?78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable synthetic linchpin, which can undergo two C?C bond-forming processes as an sp3-nucleophile, followed by a third C?C bond-forming reaction as an effective sp2-electrophile. This discovery significantly enhances the utility of this ubiquitous, but underutilized, linker group.
- Trost, Barry M.,Kalnmals, Christopher A.
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supporting information
p. 9066 - 9074
(2018/06/29)
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- Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes
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Herein, a ruthenium-catalyzed cycloisomerization that transforms 1,6-haloenynes into 5-membered carbo- and heterocycles that bear exocyclic, stereodefined, tetrasubstituted vinyl halides is reported. The reaction is insensitive to air and water, tolerates a variety of functional groups, and proceeds with good to excellent stereoselectivity and yield.
- Trost, Barry M.,Kalnmals, Christopher A.
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p. 2346 - 2349
(2017/05/12)
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- A one-pot stereoselective synthesis of electron-deficient 4-substituted (E, E)-1-arylsulfonylbuta-1,3-dienes and their chemoselective [3+2] cycloaddition with azomethine ylides - A simple synthesis of 1,3,4-trisubstituted pyrrolidines and pyrroles
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A simple and efficient method for the synthesis of (E,E)-1-(arylsulfonyl) buta-1,3-dienes bearing electron-withdrawing substituents like cyano and ethoxycarbonyl at position 4, involving a one-pot alkylation of bis(phenylsulfonyl)methane with trans-ethyl 4-bromocrotonate/trans-4- bromocrotononitrile, and elimination of arylsulfinic acid, is described. These dienes undergo facile mono [3+2] cycloaddition with azomethine ylides chemoselectivity to furnish functionalized 1,3,4-trisubstituted pyrrolidines. Oxidation of these cycloadduct with MnO2·SiO2 under mild conditions provides 1,3,4-trisubstituted pyrroles. Georg Thieme Verlag Stuttgart. New York.
- Sankar, Ulaganathan,Mahalakshmi, Susarla,Balasubramanian, Kalapattukuppuswamy
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p. 1533 - 1540
(2013/08/23)
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- Niobium(V) chloride catalyzed oxidation of dithioacetals with 30% hydrogen peroxide: A concise preparation of bissulfonylmethylene compounds
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The oxidation of dithioacetals with 16 eq of 30% hydrogen peroxide in the presence of 10 mol% niobium(V) chloride at room temperature provides bissulfonylmethylenes in high yields.
- Kirihara, Masayuki,Goto, Takumi,Noguchi, Takuya,Suzuki, Michitaka,Ishizuka, Yuki,Naito, Sayuri
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p. 460 - 463
(2013/05/22)
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- Electrophilicities of bissulfonyl ethylenes
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Kinetics of the reactions of bissulfonyl ethylenes with various carbanions, a sulfur ylide, and siloxyalkenes have been investigated photometrically at 20°C. The second-order rate constants have been combined with the known nucleophile- specific parameters N and sN for the nucleophiles to calculate the empirical electrophilicity parameters E of bissulfonyl ethylenes according to the linear free energy relationship log k(20°C)=s N(N+E). Structure-reactivity relationships are discussed, and it is shown that the electrophilicity parameters E derived in this work can be employed to define the synthetic potential of bissulfonyl ethylenes as Michael acceptors. Copyright
- Asahara, Haruyasu,Mayr, Herbert
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supporting information; experimental part
p. 1401 - 1407
(2012/07/28)
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- Fe-catalyzed allylic C-C-bond activation: Vinylcyclopropanes as versatile a1,a3,d5-synthons in traceless allylic substitutions and [3 + 2]-cycloadditions
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The low-valent iron complex Bu4N[Fe(CO)3(NO)] (TBAFe) catalyzes the allylic C-C-bond activation of electron-poor vinyl cyclopropanes to generate synthetically useful a1,a3,d5-synthons which are prone to undergo multiple consecutive reactions. The versatility of this approach is demonstrated by a traceless allylic substitution and a formal [3 + 2] cycloaddition to give either functionalized acyclic products or densely substituted cyclopentanes and pyrrolidines in high yields and regioselectivities.
- Dieskau, Andre P.,Holzwarth, Michael S.,Plietker, Bernd
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p. 5048 - 5051
(2012/05/05)
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- Nucleophilic fluoromethylation of aldehydes with fluorobis(phenylsulfonyl) methane: The importance of strong Li-O coordination and fluorine substitution for C-C bond formation
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The tighter, the better! Fluorobis(phenylsulfonyl)methane reacts readily with aldehydes to give addition products in excellent yields (see scheme; LiHMDS=lithium hexamethyldisilazide), which is in sharp contrast to previous findings. Both strong Li-O coordination at low temperature and fluorine substitution play important roles in successful C-C bond formation. Copyright
- Shen, Xiao,Zhang, Laijun,Zhao, Yanchuan,Zhu, Lingui,Li, Guangyu,Hu, Jinbo
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p. 2588 - 2592
(2011/04/25)
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- POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS
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A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising recurring units containing a non-leaving hydroxyl group represented by formula (1) wherein R1 is H, methyl or trifluoromethyl, X is a single bond or methylene, m is 1 or 2, and the hydroxyl group attaches to a secondary carbon atom. The composition is improved in resolution when processed by lithography.
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- Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging michael acceptors
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Chiral amines with a pyrrolidine framework catalyze the enantioselective conjugate addition of a broad range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99% ee. This novel process provides synthetically useful chiral γ-gem-sulfonyl or phosphonyl aldehydes which can be widely functionalized with retention of the enantiomeric excess. Mechanistic insights including DFT calculations are explored in detail.
- Sulzer-Mosse, Sarah,Alexakis, Alexandre,Mareda, Jiri,Bollot, Guillaume,Bernardinelli, Gerald,Filinchuk, Yaroslav
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supporting information; experimental part
p. 3204 - 3220
(2009/12/03)
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- [3+2] Cycloaddition of phenyliodonium bis(arylsulfonyl)methylides with α,β-enones
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The [3+2] cycloaddition of phenyliodonium bis(arylsulfonyl)methylides to α,β-enones affords exclusively trans,trans-configured 1-(arylsulfonyl)-2-aroyl-3-arylindanes. The initial electrophilic attack of the iodonium ylide on the alkenyl double bond of the chalcone, followed by cyclization of the dipolar species, and subsequent ejection of iodobenzene and sulfur dioxide, stereoselectively affords the indane cycloadduct. Georg Thieme Verlag Stuttgart.
- Adam, Waldemar,Gogonas, Efstathios P.,Nyxas, Ioannis A.,Hadjiarapoglou, Lazaros P.
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p. 3211 - 3218
(2008/09/16)
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- Nitrogen-containing organic compound, resist composition and patterning process
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Resist compositions comprising nitrogen-containing organic compounds having a benzimidazole structure and a specific ether chain moiety have an excellent resolution, form precisely configured patterns with minimized roughness of sidewalls and are useful in microfabrication using electron beams or deep-UV light.
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- Sulfonates, polymers, resist compositions and patterning process
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A sulfonate compound having formula (1) is novel wherein R1 to R3 are H, F or C1-20 alkyl or fluoroalkyl, at least one of R1 to R3 contains F. A polymer comprising units derived from the sulfonate compound is used as a base resin to formulate a resist composition which is sensitive to high-energy radiation, maintains high transparency at a wavelength of up to 200 nm, and has improved alkali dissolution contrast and plasma etching resistance
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- A novel effective electrophile: β-trifluoroacetylketene diphenyldithioacetal S,S-tetroxide
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A synthesis of a novel electrophilic reagent - β- trifluoroacetylketene diphenyldithioacetal S,S-tetroxide 3 is described. The reaction of 3 with various electron-rich aromatics such as 1,3-dimethoxybenzene, 2-methylthiophene, N-methylpyrrole, and 2-methylindole was investigated. In the course of these reactions an unusual migration of a phenylsulfonyl group takes place. An easy and ready for scale-up procedure for the synthesis of previously unknown β-aryl, α-phenylsulphonyl substituted α,β-unsaturated trifluoromethyl ketones is reported.
- Krasovsky, Arkady L.,Druzhinin, Sergej V.,Nenajdenko, Valentine G.,Balenkova, Elizabeth S.
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p. 1129 - 1132
(2007/10/03)
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- A Facile Diastereoselective Synthesis of Functionalized 1,2,3-Trisubstituted Benzocyclopentenes through the Cycloaddition of Bis(phenylsulfonyl)iodonium Ylides to Cyclic Alkenes
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The thermal cycloaddition of β-disulfonyl iodonium ylides to cyclic alkenes affords exclusively 1,2,3-trisubstituted cis(1,2)/cis(2,3)-configured benzocyclopentenes by an electrophilic attack of the ylide on the olefinic double bond. This unsual transformation provides a convenient and direct method for the diastereoselective synthesis of functionalized bicyclo [3.3.0] octanes (characteristic structural units contained in polyquinane natural products), when cyclopentenes are used as cycloalkene partner.
- Adam, Waldemar,Gogonas, Efstathios P.,Hadjiarapoglou, Lazaros P.
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p. 9155 - 9158
(2007/10/03)
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- A remarkable cycloaddition of bis(arylsulfonyl)iodonium ylide with norbornene derivatives for the direct synthesis of functionalized indanes
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The reaction of bis(arylsulfonyl)iodonium ylides with a variety of norbornene derivatives 3 affords functionalized indanes 4 in good yields through an unusual cycloaddition. This diastereoselective cycloaddition provides a convenient preparative route to multicyclic structures of well defined stereochemical configuration.
- Adam, Waldemar,Gogonas, Efstathios P.,Hadjiarapoglou, Lazaros P.
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p. 1165 - 1169
(2007/10/03)
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- A simple reduction of α-bromosulfones by cat.(PhSe)2/NaBH4
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Reduction of α-bromosulfones 1, 5, 13-16 by cat.(PhSe)2/NaBH4 occurred site-selectively in high yields. This reduction of 1,3- or 1,4-dibromobis(sulfone) 21 and 25 was applied to intramolecular coupling reactions to give the three- and four-membered carbocycles 26-28.
- Yoshimatsu, Mitsuhiro,Ohara, Megumi
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p. 5651 - 5654
(2007/10/03)
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- THE REACTION BETWEEN PHENYLIODONIUM BIS(PHENYLSULFONYL)METHANIDE AND PYRROLIDINE
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The main product from the title reaction is the enamine N--pyrrolidine, 4.Tetrakis(phenylsulfonyl)propane, 3, is a by-product, when dichloromethane is used; it is formed independently from this solvent and bis(phenylsulfonyl)methane in the presence of pyrrolidine.Key words: Phenyliodonium bis(phenylsulfonyl)methanide, N--pyrrolidine, 1,1,3,3-tetrakis(phenylsulfonyl)propane, dichloromethane, pyrrolidine.
- Nikas, Spyros,Rodios, Nestor,Terzis, Aris,Varvoglis, Anastassios
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p. 285 - 288
(2007/10/02)
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- Alkylation of Sodium Phenylsulfinate on Alumina. Activation by Microwaves or Ultrasounds.
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Organic halides absorbed without solvent onto sodium phenylsulfinate on alumina (1) gave phenylsulfones (2) under microwave or ultrasound activation.
- Villemin, Didier,Alloum, Abdelkrim Ben
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p. 925 - 932
(2007/10/02)
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- Reactivity of Phenyliodonium Bis(aryl- or alkyl-sulphonyl)methylides towards Thiobenzophenones
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Thermal reactions of several phenyliodonium bis(aryl or alkyl-sulphonyl)methylides with some thiobenzophenones are described. 4,4'-Dimethoxythiobenzophenone affords exclusively 2-arylsulphonyl-3-(4-methoxyphenyl)-6-methoxybenzothiophenes, whereas other thiobenzophenones may give also gem-bis(arylsulphonyl)thiiranes and in one case an unsaturated gem-disulphone.Some oxidation reactions of an ylide with various substrates occur either thermally or photochemically.
- Hatjiarapoglou, Lazaros,Varvoglis, Anastassios
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p. 379 - 382
(2007/10/02)
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- Stibonium and Bismuthonium Ylides. A Comparison with Arsonium and Other Ylides, also including the Crystal Structure of Triphenylarsonium Bis(phenylsulphonyl)methylide and Triphenylarsonium and Triphenylstibonium 4,4-dimethyl-2,6-dioxocyclohexylides
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The spectra, dipole moments, X-ray structures, and chemistry (stability, hydrolysis, reactivity in Wittig reactions) of a number of stibonium ylides are compared with similar properties of their arsonium analogues.There is a close resemblance between the stibonium and arsonium ylides; this is explained in terms of intramolecular interaction between substituent oxygen atoms and the antimony or arsenic atoms.Attempts to prepare stibonium ylides from dichlorotriphenylantimony(V) led always to ylides contaminated with oxybis(triphenylantimony) dichloride.Other oxybis(triphenylantimony) derivatives were obtained from acid hydrolyses of stibonium ylides.Two bismuthonium ylides were also studied.In their case also there appears to be an intramolecular bismuth-oxygen interaction.
- Ferguson, George,Glidewell, Christopher,Gosney, Ian,Lloyd, Douglas,Metcalfe, Shirley,Lumbroso, Henri
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p. 1829 - 1838
(2007/10/02)
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- REACTIVITY OF PHENYLIODONIUM BIS(ARYLSULPHONYL)METHYLIDES TOWARDS ALKENES AND ALKYNES: CRYSTAL STRUCTURE OF 9-PHENYLSULPHONYL-1,2,3,4,4a,9a-HEXAHYDRO-1,4-METHANOFLUORENE
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Thermal or photochemical reactions of phenyliodonium bis(arylsulphonyl)methylides with alkenes lead normally to gem-(arylsulphonyl)cyclopropanes.Norbornene and trans-stilbene, however, afford 1-(phenylsulphonyl)indane derivatives.The crystal structure of the title compound /= 3.0>> confirmed the identity of the product with norbornene.Diarylacetylenes give 1-(arylsulphonyl)indenes.Thermal decomposition of the ylides involves a new rearrangement, with formation of aryl arenethiosulphonates.
- Hatjiarapoglou, Lazaros,Varvoglis, Anastassios,Alcock, Nathaniel W.,Pike, Graham A.
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p. 2839 - 2846
(2007/10/02)
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- Synthese de lactones a cycle moyen: Application a la synthese du pentadecanolide-15 et du phoracantholide I
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Medium ring size lactones can be prepared from bifunctional commercial starting compounds in high yields, using a few step sequence.Lactonisation is obtained by cyclization of the free ω-hydroxyacids or by the cyclization of ω-hydroxyacids having the hydroxy and carboxy group protected.
- Cossy, Janine,Pete, Jean-Pierre
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p. 989 - 994
(2007/10/02)
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- The Reaction of Phenyliodonium Bis(phenylsulfonyl)methylide with some Thiophenes
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The title iodonium ylide gives with thiophenes C-H isertion products of the C(SO2Ph)2 group and with benzothiophenes transylidation products
- Hatjiarapoglou, Lazaros,Varvoglis, Anastasios
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p. 1599 - 1600
(2007/10/02)
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- EFFECIENT 4 + 1 SYNTHESES OF HIGHLY FUNCTIONALIZED CYCLOPENTENES
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Condensation of sulfone-activated methylene compounds with cis-1,4-dichloro-2-butene yields cyclopentenes.Elaboration of these cyclopentene products into highly functionalized intermediates is described.
- Nantz, M. H.,Radisson, X.,Fuchs, P. L.
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- The Base-catalysed Cyclisation of ο-Epoxy 1,1-Bis-sulphones. Reactivity and Selectivity as a Function of Ring Size
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Cyclisation of terminal bis-sulphones can occur in two different modes; rates of ring closure for three- to seven-membered rings span over three orders of magnitude.
- Benedetti, Fabio,Fabrissini, Silvio,Gianferrara, Teresa,Risaliti, Amerigo
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p. 406 - 407
(2007/10/02)
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- REACTION OF 1,1-BIS(PHENYLSULFONYL)ETHENE WITH AMINES
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The reactions of 1,1-bis(phenylsulfonyl)ethene with aliphatic, aromatic, and heterocyclic amines in anhydrous aprotic solvents take place in two directions, depending on the basicity of the amine.They lead to the formation of secondary 1,1-bis(phenylsulfonyl)-ethyl-N-aryl(heteryl)amines as addition products, or to 1,1,3,3-tetrakis(phenylsulfonyl)propane, or to their mixtures.By analysis of the reaction mixtures and identification of the intermediate products a scheme was proposed for the reactions of 1,1-bis(phenylsulfonyl)ethene with amines.
- Bazavova, I. M.,Neplyuev, V. M.,Lozinskii, M. O.
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- Syntheses a l'aide de sulfones. XVIII. Utilisation des disulfones-1,1 pour la synthese stereoselective de composes olefiniques
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2-Alkenyl-1,1-disulfones 4 are readily available in excellent yields by condensation of aldehydes with bisaryl or bisalkylsulfonylmethanes in the presence of piperidine acetate and molecular sieves at room temperature.A small amount of the 1-alkenyl isomer is also found when the aldehyde is α-substituted but it can be converted into the 2-alkenyl isomer by base catalysed equilibration.The 2-alkenyl-1,1-disulfones display only E geometry whereas E allylic monosulfones are difficult to isolate in a state of stereochemical purity (about 20percent of the Z isomer at equilibrium (8)).Alkylation is readily performed: treatment of 4 and 6 by sodium hydride in dimethylformamide and then by methyl iodide gives disulfones 5 E and 7 in 78-95percent yields.The alkylation of 4 (R=Et) by butyl iodide gives 70percent of 5 E(R=Et, R'=n-Bu) resulting from alkylation at the α position and 8percent of 3 (R=Et, R'=n-Bu) resulting from alkylation at the γ position.The α isomer is readily purified by crystallization.Reduction of disulfones 4 or 5 by aluminium amalgam leads quantitatively to allylic sulfones 2E or 8E.Olefins 9E are obtained upon total reduction of disulfones 4 or 5 by lithium in ethylamine at -78 deg C but in the case of disulfones 5 the olefins 9E are contaminated by isomers 10E and 10Z.
- Cuvigny, Therese,Penhoat, Catherine Herve Du,Julia, Marc
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- THIOALKYLATION. VII. CONDENSATION OF 1,3-DISULFONES WITH FORMALDEHYDE AND POTASSIUM HYDROSULFIDE
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1,1,5,5-Tetrakis(butylsulfonyl)-, 1,1,5,5,-tetrakis(cyclohexylsulfonyl)-, and 1,1,5,5-tetrakis(phenylsulfonyl)-3-thiapentanes were obtained by the reaction of bis(butylsulfonyl)-, bis(cyclohexylsulfonyl)-, and bis(phenylsulfonyl)methanes respectively with formaldehyde and potassium hydrosulfide in molar ratios of 2:2:1.
- Dronov, V. I.,Nigmatullina, R. F.,Makhmutova, I. Kh.,Nikitin, Yu. E.
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p. 468 - 470
(2007/10/02)
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- THE RECTIONS OF SOME BROMO-DERIVATIVES OF COMPOUNDS HAVING REACTIVE METHYLENE GROUPS WITH THIOUREAS, AND OF SOME RESULTANT THIOURONIUM SALTS WITH BASE
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Whereas α-bromocarbonyl compounds react with thiourea to give thiazole derivatives, bromomalononitrile and bromobis(phenylsulphonyl)methane underwent protodebromination.With N,N,N',N'-tetramethylthiourea many of the bromo compounds gave thiouronium salts but protodebromination sometimes supervened.N,N'-Disubstituted thioureas provided examples of salt formation, protodebromination and cyclisation reactions.The only thiouronium salt to provide an ylide on treatment with base was the S--N,N,N',N'-tetramethylthiouronium bromide.N,N'-Disubstituted salts gave isothioureas rather than ylides.Thiouronium dicyano methylide underwent cyclisation rather than a Wittig reaction when heated with p-nitrobenzaldehyde, and the aldehyde condensed with the resultant 2-aminothiazole.
- Lloyd, Douglas,Millar, Ross W.
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p. 2675 - 2679
(2007/10/02)
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