50344-83-7Relevant academic research and scientific papers
One-Pot Synthesis of Deuterated Aldehydes from Arylmethyl Halides
Li, Xiangmin,Wu, Shanchao,Chen, Shuqiang,Lai, Zengwei,Luo, Hai-Bin,Sheng, Chunquan
supporting information, p. 1712 - 1715 (2018/04/14)
A facile, one-pot approach for synthesizing deuterated aldehydes from arylmethyl halides was developed using D2O as the deuterium source. The efficient process is realized by a sequence of formation, H/D exchange, and oxidation of pyridinium salt intermediates. The mild and air-compatible reaction conditions enable efficient synthesis of diverse deuterated aldehydes with high deuterium incorporation.
Method for preparing deuterated aldehyde compound by using halomethyl compound as raw material
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Paragraph 0044-0045; 0047-0048, (2018/09/08)
The invention provides a method for preparing deuterated aldehyde compound by using halomethyl compound as a raw material. The method comprises the following steps that in solvent and D2O mixed liquidwith a pyridine compound, the halomethyl compound is added; reaction is performed at 0 to 100 DEG C; then, a nitrosobenzene type compound is added for continuous reaction; finally, reaction liquid issubjected to acidification to obtain a target product. The method has the advantages that the used raw materials are cheap and can be easily obtained; expensive reagents or heavy metal raw materialsare not needed; the reaction conditions are simple; the severe conditions such as high temperature are not needed; the cost of the preparation method is low; the operation is simple; the deuterated rate is high and can reach 97 percent; the target product can be easily purified; the yield is high and reaches up to 95 percent. The substrates used by the method have wide applicability; various deuterated aldehyde compounds can be prepared.
Evidence of a Nitrene Tunneling Reaction: Spontaneous Rearrangement of 2-Formyl Phenylnitrene to an Imino Ketene in Low-Temperature Matrixes
Nunes, Cláudio M.,Knezz, Stephanie N.,Reva, Igor,Fausto, Rui,McMahon, Robert J.
supporting information, p. 15287 - 15290 (2016/12/09)
Triplet 2-formyl phenylnitrene was generated by photolysis of 2-formyl phenylazide isolated in Ar, Kr, and Xe matrixes and characterized by IR, UV-vis, and EPR spectroscopies. Upon generation at 10 K, the triplet nitrene spontaneously rearranges in the dark to singlet 6-imino-2,4-cyclohexadien-1-ketene on the time scale of several hours. The intramolecular [1,4] H atom shift from the nitrene to the imino ketene occurs by tunneling, on the triplet manifold, followed by intersystem crossing. This case constitutes the first direct evidence of a tunneling reaction involving a nitrene.
Indole synthesis based on a modified koser reagent
Fra, Laura,Millán, Alba,Souto, José A.,Mu?iz, Kilian
, p. 7349 - 7353 (2014/07/21)
A new metal-free method for the rapid and productive preparation of indoles has been developed. This process is based on sterically congested hypervalent iodine compounds of the family of Koser reagents, and iodosobenzene in combination with 2,4,5-tris-isopropylbenzene sulfonic acid provides the highest yields and fastest reaction times. This reagent alone promotes the chemoselective oxidative cyclization of 2-amino styrenes to indoles in high yields under mild conditions. Convenient route to indole: A fast, productive, and operationally simple indole synthesis was developed.
An efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles via tandem reactions of 2-(gem-dibromo(chloro)vinyl)anilines with diselenides(disulfides)
Liu, Jie,Li, Pinhua,Chen, Wei,Wang, Lei
supporting information, p. 10052 - 10054 (2012/10/30)
A novel and efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl) indoles through tandem reactions of 2-(gem-dibromo(chloro)vinyl)-N- methylsulfonylanilines with diselenides and disulfides in the presence of t-BuOLi and I2 (10 mol%) in DMS
A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles
Fang, Yuan-Qing,Lautens, Mark
, p. 538 - 549 (2008/09/17)
(Chemical Equation Presented) A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline leading to indoles with group at C2-C7. The orthogonal approach of the sequential copper- and palladium-mediated synthesis of 1,2-diarylindoles exploited the wide availability of diverse organoboron reagents.
α-(METHYLTHIO)BENZYL SULFONES AS SYNTHETIC INTERMEDIATES. PART V. SYNTHESES OF SOME o- AND m-SUBSTITUTED 1-DEUTERIOBENZALDEHYDES
Wladislaw, B.,Marzorati, L.,Ebeling, G.
, p. 25 - 28 (2007/10/02)
o- and m-Substituted α-methylthiobenzyl sulfones incorporate deuterium when treated with a base and deuterium oxide.The resulting deuterated sulfones, by thermal decomposition, afford o- and m-substituted 1-deuteriobenzaldehydes in good yields and high is
Photochemistry of (2-nitrophenyl)diazomethane studied by the matrix isolation technique. (Nitrophenyl)carbene to (carboxylphenyl)nitrene rearrangement by successive reduction of the nitro group with the carbenic center
Tomioka, Hideo,Ichikawa, Naoki,Komatsu, Kazunori
, p. 8045 - 8053 (2007/10/02)
Irradiation (λ > 350 nm) of (2-nitrophenyl)diazomethane (1) matrix-isolated in Ar at 10 K provided 2-nitrosobenzaldehyde (3) presumably as a result of intramolecular oxygen migration in (2-nitrophenyl)carbene (2). Upon further irradiation (λ > 350 nm), 3 was decomposed to give a mixture of 2,1-benzisoxazol-3(1H)-one (4) and carbonylcyclopentadiene imine (5) along with CO2. The oxazolone (4) underwent decarboxylation to give 5 upon irradiation with shorter wavelength light (λ > 300 nm) but not at longer wavelength (λ > 350 nm), suggesting 4 is not the direct precursor for 5 in the photolysis of 3. Irradiation (λ > 350 nm) of (4-n-butyl-2-nitrophenyl)diazomethane (1b) under similar conditions resulted in the formation of carbonyloximinocyclohexadienylidene (7) which then produced the oxazolone (4b) and the imine (5b) upon further irradiation, suggesting that a 1,4-biradical generated as a result of abstraction of H at the ortho position by the photoexcited nitroso group was involved in the reaction of 3 forming 4. (2-Carboxyphenyl)nitrene (9) generated by 1,4-OH shift in the 1,4-biradical was postulated as an intermediate leading to 5, and this was actually demonstrated by independent generation of 9 by the photolysis of 2-azidobenzoic acid (8).
