6335-78-0Relevant articles and documents
PhI(OAc)2-mediated alkoxyoxygenation of β,γ-unsaturated ketoximes: Preparation of isoxazolines bearing two contiguous tetrasubstituted carbons
Ye, Chenghao,Kou, Xuezhen,Yang, Guoqiang,Shen, Jiefeng,Zhang, Wanbin
supporting information, p. 1148 - 1152 (2019/03/26)
A PhI(OAc)2-promoted dioxygenation of allyl oximes, including one alkoxylation, has been developed. This reaction can give isoxazoline products bearing two contiguous tetrasubstituted carbons. Various oximes substrates bearing different aryl groups and tetrasubstituted-olefin moieties were compatible with the mild reaction conditions. A two-electron oxidation pathway was proposed based on results of preliminary mechanistic studies.
Palladium(0)-Catalyzed Coupling Reaction of Lithium (α-Carbalkoxyvinyl)cuprates with Organic Halides
Tsuda, Tetsuo,Yoshida, Tsutomu,Saegusa, Takeo
, p. 607 - 610 (2007/10/02)
The palladium(0)-catalyzed coupling reaction of lithium (α-carbalkoxyvinyl)(dicyclohexylamido)cuprates and organic halides such as aryl, vinyl, and benzyl halides was investigated.The lithium (α-carbalkoxyvinyl)dicyclohexylamido)cuprates were generated by conjugate addition of organo(dicyclohexylamido)cuprates to α,β-acetylenic esters.The coupling reaction using a Pd(PPh3)4 catalyst proceeded at room temperature to give synthetically useful α,β-substituted acrylates in good yields.The coupling reaction of the (α-carbalkoxyvinyl)(dicyclohexylamido)cuprate derived from a β-unsubstituted α,β-acetylenic ester took place stereoselectively to give an (E)-α,β-substituted acrylate derivative.In the vinyl halide reaction, the stereochemistry of the vinyl halide component is retained in the coupling product.The use of the dicyclohexylamido group as a nontransferable ligand is important.Thus, in the reaction using an (α-carbalkoxyvinyl)(1-hexynyl)cuprate complex, a nonselective coupling involving the 1-hexynyl group took place.
ETUDE DE LA REACTION CHLOROCARBENE-ACETALS DE CETENES. I. SYNTHESE D'ESTERS α,β-ETHYLENIQUES.
Slougui, N.,Rousseau, G.
, p. 2643 - 2652 (2007/10/02)
The reaction of chloro, chloromethyl and chlorophenyl carbenoids with ketene alkylsilylacetals has been studied.Excellent yields of cyclopropanation were observed and the unstable chlorocyclopropanone acetals formed were thermally rearranged in high yield into α-substituted α,β-ethylenic esters.This new method for the synthesis of unsaturated esters appeared complementary of the known-ones.
AN INTERPRETATION OF THE SUBSTITUENT EFFECT IN THE BLAISE REARRANGEMENT IN TERMS OF PI-ORBITALS
Abe, Yukio,Suehiro, Tadashi
, p. 389 - 392 (2007/10/02)
The migratory aptitude of the substituent groups in the Blaise rearrangement can be explained in terms of the pi-electronic properties of the groups in the highest occupied molecular orbitals.The rates of the rearrangement reaction with relation to the substituent groups were also rationally understood based on the energy levels of the molecular orbitals.
FORMATION OF CYCLOPROPANE DERIVATIVES IN THE BLAISE REARRANGEMENT
Abe, Yukio,Suehiro, Tadashi
, p. 337 - 340 (2007/10/02)
On heating tosylates of ethyl 2-alkyl-2-methyl-3-hydroxy-3-phenylpropanoate (R=Me, 1b; R=Et, 6) in o-dichlorobenzene at 170 deg C, ethyl 1- methyl-2-phenyl- and 1,2-dimethyl-3-phenylcyclopropanecarboxylates, 3, and 8, were formed in both 5percent yield, respectively, whereas the alkyl migration products, ethyl 3-alkyl-2-methyl-3-phenylpropenoates, were not produced.The mode of the reaction of the methyl group with the cationic carbon was described.
Unambiguous Proof for Alcoxycarbonyl-group Migration in Wagner-Meerwein Rearrangements
Berner, Daniel,Dahn, Hans,Vogel, Pierre
, p. 2538 - 2553 (2007/10/02)
In HSO3F/SO2ClF the β-hydroxy esters Ph-CHOH-CMe2-COOR (1, R=Me, Et) are doubly protonated, then transformed into the fluorosulfates 7 and (partly) into the fluorides 8.At -15 deg C, both 7 and 8 undergo a rearrangement, forming derivatives of Me2C=C(Ph)C
