31802-10-5Relevant academic research and scientific papers
Rhodium-catalyzed oxidative ortho -acylation of benzamides with aldehydes: Direct functionalization of the sp2 C-H bond
Park, Jihye,Park, Eonjeong,Kim, Aejin,Lee, Youngil,Chi, Ki-Whan,Kwak, Jong Hwan,Jung, Young Hoon,Kim, In Su
supporting information; experimental part, p. 4390 - 4393 (2011/10/08)
A rhodium-catalyzed oxidative acylation of benzamides with aryl aldehydes via direct sp2 C-H bond cleavage is described. In the presence of [Cp*RhCl2]2, AgSbF6, and silver carbonate as an oxidant, N,N-diethyl be
Pseudoacids. II. 2-Acylbenzoic Acid Derivatives
Valente, Edward J.,Martin, Samuel B.,Sullivan, Larry D.
, p. 264 - 276 (2007/10/03)
Structures of derivatives of cyclic o-acylbenzoic acids, including the chloride, endo- and exocyclic amides, esters and anhydrides, are examined. 3-Chloro-1(3H)-isobenzofuranone (1), orthorhombic, Pbca, a = 11.616 (5), b = 8.120 (3), c = 15.640 (9) A; 3-methoxy-3-phenyl-1(3H)-isobenzofuranone (3), orthorhombic, P212121, a = 6.923 (2), b = 8.291 (4), c = 21.551 (8) A; 3-hydroxy-3-phenyl-N-propyl-1(3H)-isoindolone (4), orthorhombic, P212121, a = 8.662 (4), b = 9.551 (7), c = 17.649 (14) A; 3-(N-morpholino)-1(3H)-isobenzofuranone (5), triclinic, P1, a = 6.172 (4), b = 11.163 (7), c = 17.33 (2) A, α = 105.91 (6), β = 99.85 (6), γ = 97.57 (5)°; 3-(2′-benzoylbenzoyloxy)-3-phenyl-1(3H)-isobenzofuranone (7), triclinic, P1, a = 9.694 (3), b = 10.505 (4), c = 11.163 (4) A°, α = 80.58 (3), β = 80.41 (3), γ = 76.49 (3)°; bis[1(3H)-isobenzofuranone-3-yl]ether (8), monoclinic, I2/a, a = 15.31 (2), b = 6.111 (12), c = 28.30 (5) A, β = 101.61 (12)°. An open oxoacid tertiary amide is also described: N-morpholino 2′-benzoylbenzamide (6): monoclinic, P21/c, a = 6.844 (4), b = 15.696 (8), c = 14.154 (7) A, β = 99.43 (4)°. Pseudoacid derivatives form planar isobenzofuran and isoindole rings, and the former aldehyde/ketone carbon-heteroatom endocyclic and exocyclic bond distances show bond length variations which correlate with the relative basicities of the attached groups. Structures of both endocyclic and exocyclic nitrogen pseudoamides are reported as well as examples of the normal-pseudoanhydride and the dipseudoanhydride.
Effect of Nucleophilicity and Leaving Group Ability on the SN2 Reactions of Amines with (Acyloxy)alkyl α-Halides: A Product Distribution Study
Sloan, Kenneth B.,Koch, Suzanne A. M.
, p. 635 - 640 (2007/10/02)
The course of the reaction of amines with (acyloxy)alkyl α-halides has been found to depend on the nucleophilicity of the amines and the leaving group ability of the halides.More nucleophilic amines tended to give acylated products 2 from the reaction while less nucleophilic amines gave alkylated products 3.The use of a better leaving group also tended to favor the formation of a greater amount of alkylated product.These results have been compared to the observations of Westaway on the effect of leaving group ability and nucleophilicity on the bond lengths in the transit ion state of SN2 reactions.In addition, secondary amines have been shown to cause the rearrangement of 2-formylbenzamides to 3-amino-1(3H)-isobenzofuranones.
