5633-67-0Relevant articles and documents
Generation of the Selenonium Ylide by the Carbenic Reaction. Formation of Cyclopropane Derivatives via Selenonium Ylide
Ibata, Toshikazu,Kashiuchi, Makoto
, p. 929 - 930 (1986)
The Cu(acac)2-catalyzed decomposition of α-diazoacetophenones in the presence of bis(p-methoxy-phenyl) selenide (3) did not give the corresponding selenonium ylide but gave r-l,c-2,t-3-tribenzoylcylopropanes through the successive reaction of the intermed
Palladium-catalyzed suzuki-miyaura cross-coupling of a-halomethyl oxime ethers and site-selective cross-coupling of dihalo derivatives
Noverges, Barbara,Mollar, Cristian,Medio-Simon, Mercedes,Asensio, Gregorio
, p. 2327 - 2342 (2013/10/01)
The cross-coupling reaction of chloro- and bromomethyl oxime ethers with a wide range of aryl-, heteroaryl- and vinylboronic acids in the presence of catalytic palladium complexes with different phosphines has been carried out with good yields (60-98%, 40 examples). Regioselective cross-coupling reactions differentiating between an alkyl or aryl position are achieved from dihalo oxime ethers containing Csp2- and Csp3-halogen bonds using mono- or dicoordinated palladium catalysts such as Pd (dba)2/P (o-tolyl)3 or Pd (PPh3)4. The selective orthogonal functionalization of dihalo oxime ethers is also described. Site-selective transformations allow the introduction of the biaryl motif into dihalo oxime ethers preserving the highly activated alkyl halide moiety vicinal to the oxime group for further transformations. In this context, Z- and E-oxime ethers could be considered as synthetic equivalents of ketones in palladium-catalyzed Suzuki reactions.
Synthesis of 2-benzoyl-3-aryl-N-arylsulphonylaziridines from the reaction of N-arylsulphonylimines with dimethylsulphonium phenacylide - The first example of a functionalized-methylene transfer to azomethines
Nadir,Arora
, p. 2355 - 2361 (2007/10/03)
The first example of phenacyl group transfer from dimethylsulphonium phenacylide to N-arylsulphonylimines to yield 2-benzoyl-1-arylsulphonylaziridines is described.
2-(Tosylamino)benzyltrimethylammonium halides as precursors of 2-substituted indoles
Croce, Piero Dalla,Ferraccioli, Raffaella,La Rosa, Concetta
, p. 2397 - 2407 (2007/10/03)
The reactions of 2-(tosylamino)benzyltrimethylammonium halides (1) with dimethylsulfonium 2-oxo-2-phenylethylide (6b), dimethylsulfonium 2-ethoxy-2-oxo-ethylide (6c) and dimethylsulfonium cyanomethylide (6d) are useful synthetic routes to 2-substituted indoles (8b-d). The relationship between reaction conditions and selectivity is discussed.
Triphenylbismuthonium 2-Oxoalkylide, A Moderately Stabilized Bismuthonium Ylide: Generation and Reactions with Some Electrophiles
Matano, Yoshihiro
, p. 2703 - 2710 (2007/10/02)
Treatment of (2-oxoalkyl)triphenylbismuthonium tetrafluoroborates 3 with potassium tert-butoxide in tetrahydrofuran at -78 deg C produced triphenylbismuthonium 2-oxoalkylides 4, which readily underwent epoxidation with the aldehydes 5 to give the α,β-epoxy ketones 7 with highly trans selectivity.The ylide 4a reacted with dimedone 11, the sulfonic acid 13, the thiol 15 and the isocyanate 17 to afford the corresponding ketones 12, 14, 16 and 19 in moderate to good yields.Reaction of the ylide 4c with the α,β-unsaturated ketones 10 and 21 afforded the 1,2-dibenzoyl- and the 1,2,3-tribenzoyl- cyclopropanes 20 and 22, respectively, although the yields were low.In the presence of a catalytic amount of nitrosobenzene 23, the ylide 4a a unique decomposition to give the 2,2,7,7-tetramethyloct-4-ene-3,6-dione 24 in quantitative yield, while the reaction with the nitrile oxide 25 yielded the isoxazoline 26.In all of these reactions, triphenylbusmuthane 6 was the additional major product.
SYNTHESIS AND SOME REACTIONS OF INDOLO-1,4-OXAZINIUM PERCHLORATES
Kibal'nyi, A.V.,Nikolyukin, Yu.A.,Dulenko, V.I.
, p. 895 - 900 (2007/10/02)
The reaction of acyl perchlorates with 1-phenacylskatole affords the previously unknown 1-R-10-methyl-3-phenylindolo-1,4-oxazinium salts, which undergo recyclization by the action of ammonia to the corresponding indolopyrazines.It is found t
Synthesis of Enones and Cyclopropanes by the Reaction of Telluronium Ylides Generated from Bis(2-oxoalkyl)tellurium Dichlorides
Han, Li-Biao,Kambe, Nobuaki,Ryu, Ilhyong,Sonoda, Noboru
, p. 561 - 564 (2007/10/02)
The reaction of bis(2-oxoalkyl)tellurium dichlorides (1) with a base gave either 1,4-dioxo-2-alkenes or 1,2,3-triacylcyclopropanes depending on the conditions employed.The reaction of 1 with LDA followed by the addition of an aldehyde led to the Wittig-type olefination to give E-α,β-unsaturated ketones in good yields.The cyclopropanes and 1,4-dioxo-2-alkenes could also be synthesized conveniently by a one-pot procedure from the corresponding ketones by the aid of TeCl4 and LDA.
A convenient synthesis of 1,t-2,c-dibenzoyl-3-(aroyl)- and (heteroaroyl)cyclopropanes by reaction of arylacyl bromides with trans-1,2-dibenzoylethylene in the K2CO3/DMF system
Saba, Antonio
, p. 55 - 56 (2007/10/02)
Treatment of α-bromo ketones 1 and trans-1,2-dibenzoylethylene with K2CO3 in DMF resulted in a selective cycloaddition affording 1,t-2,c-dibenzoyl-3-(aroyl)- and -(heteroaroyl)cyclopropanes 2
trans-1,2,3-Tris(aroyl)- and trans-1,2,3-Tris(heteroaroyl)-cyclopropanes via Cyclotrimerization of α-Bromo ketones in the System K2CO3/DMF.
Saba, Antonio
, p. 2227 - 2242 (2007/10/02)
Treatment of α-bromoketones (1) with K2CO3 in DMF resulted in a deviation from the expected Darzens-type condensation affording exclusively trans-1,2,3-trisubstituted cyclopropanes (3).
Cyclic Selenonium exo-Ylides (3,4-Dihydro-1H-2-benzoselenin-2-io)methanides; Syntheses and Reactions
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Tsutsumi, Kazuhiro,Hu, Yong-Zhou,Nishigiri, Motoo
, p. 39 - 45 (2007/10/02)
Stable cyclic selenonium exo-ylides (3,4-dihydro-1H-2-benzoselenin-2-io)methanides; (5a-e) have been synthesized by reactions of 3,4-dihydro-1H-2-benzoselenin-2,2-dichloride (4) or N-(3,4-dihydro-1H-2-benzoselenin-2-io)toluene-p-sulphonamidate (6) and active methylene compounds.The ylidic nature and the stable configuration of (5a-e) were established on the basis of their spectral data.The reactions of ylides having acetyl group(s) (5a,b) with dimethyl acetylenedicarboxylate afforded the furan derivatives (8a,b) and (9a) and the dihydrobenzoselenin (3), while reactions of the ylides having no acetyl group, (5c-e), afforded the benzoselenonines (14c-e).The diacetylmethanide (5a) when heated gave the benzoselenepine (15), while (5c) when heated afforded the styrene derivative (18) and a tetrasubstituted ethylene (19).When heated, (5d) gave the rearranged product (22). 3,4-Dihydro-1H-2-benzoselenin-2-io)phenacylide (31) was generated by the reaction of the selenonium salt (24) with sodium hydride but was too unstable to be isolated.Thermal decomposition of (31) yielded (3), its counterparts (26-28), a styrene derivative (25), and a novel rearrangement product (29).
