51075-22-0Relevant academic research and scientific papers
The reaction of cyclopropanols with Burgess reagent: A reinvestigation and correction
Banert, Klaus,Ries, Monika,Schaumann, Ernst
, p. 205 - 212 (2011)
Chemical Equation Presented The reaction of cyclopropanols with Burgess reagent yields the unusual sulfamates 8 and their N-methylated derivatives 9. Unlike a previous study, dicyclopropyl ether formation was not observed. Also, the mechanism of ether formation from a cyclopropanol precursor cannot follow an SN2 pathway with retention. Copyright Taylor & Francis Group, LLC.
N-Heterocyclic carbene-mediated organocatalytic transfer of tin onto aldehydes: New access to α-silyloxyalkylstannanes and γ- silyloxyallylstannanes
Blanc, Romain,Commeiras, Laurent,Parrain, Jean-Luc
supporting information; experimental part, p. 661 - 666 (2010/06/19)
A new, highly efficient and mild N-heterocyclic carbene (NHC)-mediated organocatalytic procedure for the transfer of tin from tributyl(trimethylsilyl) stannane (Bu3SnSiMe3) onto aldehydes for the preparation of α-silyloxyalkylstannanes and γ-silyloxyallylstannanes has been developed.
Enantioselective synthesis of allenamides via sulfimide [2,3]-sigmatropic rearrangement
Armstrong, Alan,Emmerson, Daniel P.G.
supporting information; experimental part, p. 1547 - 1550 (2009/09/06)
Chiral allenamides are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of propargylic sulfimides. The required branched propargylic sulfides are prepared by an enantioselective organocatalytic aldehyde α-sulfenylation followed by Corey-Fuchs alkynylation.
Reactions of perfluoroalkanesulfonyl chlorides with silyl enol ethers catalyzed by a ruthenium(II) phosphine complex
Kamigata, Nobumasa,Udodaira, Kumiko,Shimizu, Toshio
, p. 155 - 168 (2007/10/03)
Reactions of trifluoromethane- and tridecafluorohexanesulfonyl chlorides with silyl enol ethers have been investigated in the presence of a ruthenium(II) phosphine complex. Perfluoroalkylation and chlorination occurred depending on the substituent of silyl enol ether; i.e. perfluoroalkylated compound was selectively obtained in the reactions with silyl enol ether possessing an electron-withdrawing group, on the other hand, chlorinated compounds selectively formed in the reaction with a silyl enol ether possessing electron-donating group.
Synthesis and isolation of α-oxo sulfines
Damen, Theodorus J. G.,Zwanenburg, Binne
, p. 319 - 320 (2007/10/03)
The synthesis of several α-oxo sulfines is discribed. Various α-oxo sulfines can be isolated as such. The Diels-Alder reaction of these sulfines with 1,3-dienes can be catalyzed by Lewis acids.
Oxymethylation of alkyliron complex CpFe(CO)2-R with hydrostannane and -silane, leading to R-CH2OH derivatives: Related reactions of CpFe(CO)(L)-R and CpFe(CO)(L)-C(O)R type organoiron complexes and the molecular structure of trans-CpFe(H)(CO)(SnPh3)2
Akita, Munetaka,Oku, Tomoharu,Tanaka, Masako,Moro-oka, Yoshihiko
, p. 3080 - 3089 (2008/10/08)
Thermal reaction of an alkyliron complex CpFe(CO)2-R (1) (R = CH2CH2Ph) and acyliron complexes, CpFe(CO)2-C(O)R (3) and CpFe(CO)(PPh3)-C(O)R (4) with 3 equiv of HMMe3 (M = Sn, Si) affords the oxymethylated product R-CH2OX (5) in excellent yields accompanied by the formation of CpFe(H)-(L)(MMe3)2 (9a L = CO, M = Sn; 10a L = CO, M = Si; 11 L = PPh3, M = Sn). The reaction of a phosphine-substituted alkyliron complex CpFe(CO)(PPh3)-R (2) under similar reaction conditions gives R-H (7). On the other hand, irradiation of the organoiron complexes 1-4 in the presence of HMMe3 produces 7 as a major product with the exception of 3 + HSnMe3 where R-CHO (6) is obtained. The thermal reaction is found to consist of two consecutive reactions, i.e., formation of 6 and reduction of 6 to 5. When HSnMe3 is used as a limiting substrate (HSnMe3/1 ≤ 2), R-CHO is actually formed in good yield. The second step is proved to be catalyzed by various iron complexes such as 9a, Fp-Me, Fp-C(O)Me, and Fp2. The relationship among 1-4 and the coordinatively unsaturated species is also discussed. The molecular structure of trans-CpFe(H)(CO)SnPh3)2 (9c) obtained by the thermal reaction of 1 with HSnPh3 has been determined by X-ray diffraction study. The unit cell contains two crystallography independent molecules with the essentially same geometry. The structure is described as a four-legged piano stool structure with the two SnPh3 groups occupying the mutually trans basal positions. The contribution of the η2-coordination mode of the H-Sn bond may be negligible on the basis of the molecular structure as well as the small 2J(H-Fe-Sn) values. Crystal data for 9c: space group P1, a = 16.248 (7) A?, b = 19.646 (6) A?, c = 11.443 (5) A?, α = 93.32 (3)°, β = 93.67 (4)°, γ = 97.09 (3)°, V = 3609 (3) A?3, Z = 4, R = 0.0312, Rw = 0.0379.
Oxymethylation of Iron Complexes with HMMe3 (M = Sn; Si, cp = C5H6) leading to R-CH2OH via a Formylation-Hydrometallation Sequence
Akita, Munetaka,Oku, Tomoharu,Moro-oka, Yoshihiko
, p. 1790 - 1792 (2007/10/02)
Thermal reaction of (cp)Fe(CO)2(R), (cp)Fe(CO)2(COR), and (cp)Fe(CO)(PPh3)(COR) (cp = C5H5) with 3 equivalents of trimethyl-stannane or -silane, affords R-CH2OH (or R-CH2OSiMe3) and (cp)Fe(CO)H(MMe3)2 in good yields; the reaction sequence follows initial reduction of transient co-ordinatively unsaturated acyl species to give the aldehyde and successive hydrometallation by the action of Me3M-Fe intermediates.
Pyridylseleno Group in Organic Synthesis. Preparation and Oxidation of α-(2-Pyridylseleno) Carbonyl Compounds Leading to α,β-Unsaturated Ketones and Aldehydes
Toshimitsu, Akio,Owada, Hiroto,Terao, Keiji,Uemura, Sakae,Okano, Masaya
, p. 3796 - 3800 (2007/10/02)
α-(2-Pyridylseleno) carbonyl compounds (A) were prepared by the reaction of ketones or aldehydes with 2-pyridylselenenyl bromide under various conditions (acidic, basic, or after conversion to silyl enol ethers) in good to excellent yields.Oxidation of A thus prepared affords α,β-unsaturated carbonyl compounds in excellent yields even in the cases where satisfactory results were not obtained by the oxidation of the corresponding α-phenylseleno carbonyl compounds.These results indicate that the 2-pyridylseleno group is a better leaving group than the phenylseleno group in selenoxide elimination leading to enones.
