78108-43-7Relevant academic research and scientific papers
Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source
Konishi, Hideyuki,Nagase, Hiroki,Manabe, Kei
supporting information, p. 1854 - 1857 (2015/01/30)
Various cyclic carbonyl compounds were concisely synthesized by carbonylative cyclization of haloarenes bearing nucleophilic moieties under Pd catalysis. A broad substrate scope and a feasible large-scale synthesis clearly demonstrate the high applicability of the reaction as a general, user-friendly method for access to cyclic carbonyl compounds.
Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride
Hiroya, Kou,Jouka, Rumi,Kameda, Mitsuyoshi,Yasuhara, Akito,Sakamoto, Takao
, p. 9697 - 9710 (2007/10/03)
The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested.
Spiro-λ4-sulfanes with intramolecular sulfur-oxygen interactions: Syntheses and molecular structures
Szabo,Kuti,Kapovits,Rabai,Kucsman, A.,Argay,Czugler,Kalman,Parkanyi
, p. 1 - 16 (2007/10/03)
Three novel N-acetylated spiro-λ4-sulfanes with five-membered spirorings (fused with aromatic rings) and with two N heteroatoms (in (1)) or with N and O heteroatoms (in (2) and (3)) in axial positions have been prepared and their molecular structures determined by X-ray diffraction. The molecular structures of compounds (1-3) show trigonal bipyramidal geometry about the central sulfur atom. The rather long axial S-N bonds(1.93 A)in he symmetric spiro-λ4-sulfane (1) exhibit the usual hypervalent character, whereas the S-N (1.73 and 1.80 A) and S-O (2.23 and 2.07 A) bond lengths in the unsymmetric spiro λ4-sulfanes (2) and (3) correspond to elongated covalent S-N bonds and highly polarized S-O hypervalent bonds, respectively. Each structure exhibits usual S-C(ar) bond lengths (1.79-1.81 A). The axial N-S-N/O and the equatorial C(ar)-S-C(ar) angles lie in the intervals 173-179°and 98-103°, respectively. The conformations of (1-3) including the single-cis-single-trans isomerism of the endocyclic and exocyclic amide parts, the shape of the spirorings, and the relative positions of the equatorial aromatic rings are discussed in detail. In (1-3) the exocyclic carbonyl-oxygen approaches the central sulfur atom by 2.90,2.73 and 2.71 A, respectively, leading to an effective intramolecular sulfur-oxygen interaction of 1,4-type. The S···O close contacts, however, do not alter appreciably the trigonal bipyramidal geometry about the central sulfur atom.
Synthesis of Novel Phosphorus Heterocycles: 2-Aryl-1-methyl-2,3-dihydro-1H-2,1-benzazaphosphole 1-Oxides
Miles, J. A.,Grabiak, R. C.,Beeny, M. T.
, p. 3486 - 3492 (2007/10/02)
A class of novel phosphorus heterocycles, 2-aryl-1-methyl-2,3-dihydro-1H-2,1-benzazaphosphole 1-oxides (1), has been prepared, beginning with the nickel-catalyzed Arbuzov reaction of diethyl methylphosphonite and o-iodotoluene and ending with an intramole
