699-73-0Relevant articles and documents
Silver-Promoted Radical Ring-Opening/Pyridylation of Cyclobutanols with N-Methoxypyridinium Salts
Chen, Yu,Zhang, Guang-Yi,Guo, Chan,Lan, Ping,Banwell, Martin G.,He, Yu-Tao
supporting information, (2022/03/03)
The silver-promoted reaction of tertiary cyclobutanols with N-methoxypyridinium salts enables the efficient synthesis of a range of C2-substituted pyridines. The overall process likely occurs by ring-opening (via β-scission) of the cyclobutoxy radical to generate the corresponding γ-keto alkyl radical that itself adds to the pyridinium salt. A wide range of tertiary cyclobutanols and N-methoxypyridinium salts are compatible with the reaction conditions.
Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp3-sp2 Coupling of Medicinally Relevant Fragments
Croft, Rosemary A.,Dubois, Maryne A. J.,Boddy, Alexander J.,Denis, Camille,Lazaridou, Anna,Voisin-Chiret, Anne Sophie,Bureau, Ronan,Choi, Chulho,Mousseau, James J.,Bull, James A.
supporting information, p. 5385 - 5395 (2019/06/24)
gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4-diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions.
Surface photochemistry: the photolysis of α-methoxy acetophenones on silica gel
Mayo, Paul de,Ramnath, N.
, p. 1293 - 1296 (2007/10/02)
The photolysis of α-methoxy acetophenones 1a-1e adsorbed on silica gel show a significant deviation from the course of reaction in methanol.The results are discussed in terms of conformational control and restricted movement of the radical through adsorption on silica gel.Factors affecting the efficiency of modification of photochemical reactivity on silica gel surface have been examined.