21906-34-3Relevant academic research and scientific papers
Transition-Metal-Free Site-Selective γ-C(sp2)-H Monoiodination of Arenes Directed by an Aliphatic Keto Group
Bian, Hong-Li,Tang, Shi-Zhong,Chen, Meng-En,Zhang, Xiao-Ming,Lv, Jian-Wei,Chen, Xiao-Wei,Qi, Feng-Ming,Chen, Shi-Wu,Zhang, Fu-Min
, p. 5314 - 5319 (2020)
A general γ-C(sp2)-H iodination method directed by an aliphatic keto group has been developed under transition-metal-free conditions for the first time, generating iodoarenes in good to excellent yields with excellent site selectivity. This protocol features a wide range of aryl-substituted ketones, short reaction times, mild reaction conditions, and scalable synthetic procedures. A possible reaction mechanism was also proposed based on several control experiments.
Aromatic ring ortho-iodoalkanone and synthesis method and application thereof
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Paragraph 0272-0277, (2020/06/22)
The invention discloses aromatic ring ortho-iodoalkanone and a synthesis method and application thereof. The structural formula of the aromatic ring ortho-iodoalkanone is shown in the specification, Ais alkyl or a 5-12-membered ring, R is alkyl, halogen, alkoxy or aryl and R' is hydrogen, alkyl, alkoxy, aryl, substituted aryl or condensed aromatic ring. The synthesis method comprises the step ofreacting with an iodination reagent in the presence of an oxidant to obtain the aromatic ring ortho-iodoalkanone. According to the method, the cheap high-valence iodine reagent is used as an oxidizingagent, the synthesis of the aromatic ring ortho-iodoalkanone can be economically and efficiently realized, the reaction process is simple, safe and easy to operate, the synthesis yield is high, and the method is suitable for industrial production.
Mass spectrometric investigations on phenylacetic acid derivatives, IV: Loss of ortho-substituents from ionized phenyl-2-propanones upon electron impact
Striegel,Mayer,Wiegrebe,Schlunegger,Siegrist,Aebi
, p. 751 - 760 (2007/10/02)
In the gas phase, the phenyl-2-propanone molecules 2a-4a lose upon electron impact chloro-, bromo-, and iodo-radicals specifically at the orthopOsition of the phenyl group giving rise to strong (M-Hal.)+-ions (70/12 eV; 1st and 2nd FFR) of identical structure as confirmed by their MIKE-CAD-spectra. The daughter ions at m/z 133 from o-chlorophenyl-2-propanone (2a) and 2,2-dimethyl-2,3-dihydro[b]furane (11) are structurally similar but not identical (similarity index 99.8). The collisionally activated (2nd FFR) (M-Br.)+-ions from o-bromophenyl-2-propanone (3a) and 1-bromo-1-phenyl-2-propanone (12) produce virtually congruent spectra. The most impOrtant subsequent fragmentation of the (M-Hal-)+-ions from 2a-4a is the loss of CO which incorporates the C-atom of the carbonyl group exclusively (13C labelling). Mechanistic aspects of the fragmentation sequences are discussed (Figs. 5 and 8).
Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio
Negishi, El-Ichi,Coperet, Christophe,Sugihara, Takumichi,Shimoyama, Izumi,Zhang, Yantao,Wu, Guangzhong,Tour, James M.
, p. 425 - 436 (2007/10/02)
The Pd-catalyzed carbonylative cyclization reaction involving ω-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-
SYNTHESIS OF ENOL ESTERS AND ENOL LACTONES VIA PALLADIUM-CATALYZED CARBONYLATION OF ARYL AND ALKENYL HALIDES
Shimoyama, Izumi,Zhang, Yantao,Wu, Guangzhong,Negishi, Ei-ichi
, p. 2841 - 2844 (2007/10/02)
Acylpalladium species derivable via oxidative addition of a Pd-phosphine complex with aryl and alkenyl iodides and CO insertion can react, either intramolecularly or intermolecularly, with enolates generated in situ to give the corresponding enol esters a
Synthesis and Solvolysis of (Z)/(E)-1-Methyl-2-vinyl Triflate and 1-Methylene-2-ethyl Triflate
Bleckmann, Wolfgang,Hanack, Michael
, p. 3021 - 3033 (2007/10/02)
The synthesis and solvolysis of the triflates (Z)/(E)-8 and 20 in various solvents are described.The (E)-triflate 8 reacts in trifluoroethanol by rearrangement via the intermediate naphthyl cation 9 to give the naphthyl ether 22 and the naphthyl triflate
