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Volumn 56, Issue 14, 2015, Pages 1904-1907

Ether derivatization via two-step protocol comprised of photochemical ethereal C-H bond chlorination and nucleophilic substitution

Author keywords

Carbon tetrachloride; Chlorination; Ether; Photoreaction; Sulfamoyl chloride

Indexed keywords

CARBON; CHLORINE; ETHER; HYDROGEN; OXYGEN; SULFUR;

EID: 84925541364     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.02.102     Document Type: Article
Times cited : (16)

References (42)
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    • For a recent review on the C-H functionalization strategy in synthesis, see
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    • For other recent reports on C-H functionalization using photoactivated ketone, see: (a)
    • For other recent reports on C-H functionalization using photoactivated ketone, see: (a) T. Kamon, Y. Irifune, T. Tanaka, and T. Yoshimitsu Org. Lett. 13 2011 2674
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    • The bond dissociation energy of propane [CH3CH2CH3] is 98.1 kcal/mol and that of diisopropyl ether [(CH3)2CHOCH(CH3)2] is 93.9 kcal/mol, see: CPC Press Boca Taton p 20 and p 74
    • The bond dissociation energy of propane [CH3CH2CH3] is 98.1 kcal/mol and that of diisopropyl ether [(CH3)2CHOCH(CH3)2] is 93.9 kcal/mol, see: Y.-R. Luo Comprehensive Handbook of Chemical Bond Energies 2007 CPC Press Boca Taton p 20 and p 74
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    • Sulfonyl chlorides are generally employed as a chlorinating agent in radical chemistry, see: (a)
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    • Many examples of related acetal formations have been reported, however starting ethers were generally restricted to tetrahydrofuran and tetrahydropyran, see: (a)
    • Many examples of related acetal formations have been reported, however starting ethers were generally restricted to tetrahydrofuran and tetrahydropyran, see: (a) A.S. Atavin, A.N. Mirskova, E.F. Zorina, and T.S. Proskurina Khim. Geterotsikl. Soedin. 12 1973 1611
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    • For photoinduced [2+2] cycloadditions, see: (a) Wiley-VCH Weinheim Chapters 5 and 7
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    • The ether chlorination was unambiguously confirmed by monitoring the reaction of THF 1b with Me2NSO2Cl. The characteristic signal of α-chlorotetrahydrofuran 2b was observed at 6.34 ppm (br d, J = 3.0 Hz) in the 1H NMR chart of the crude reaction mixture. Further treatment with p-nitrobenzyl alcohol/ppts furnished the adduct 3b along with disappearance of 2b. For NMR data of α-chlorotetrahydrofuran, see
    • The ether chlorination was unambiguously confirmed by monitoring the reaction of THF 1b with Me2NSO2Cl. The characteristic signal of α-chlorotetrahydrofuran 2b was observed at 6.34 ppm (br d, J = 3.0 Hz) in the 1H NMR chart of the crude reaction mixture. Further treatment with p-nitrobenzyl alcohol/ppts furnished the adduct 3b along with disappearance of 2b. For NMR data of α-chlorotetrahydrofuran, see: K. Cai, Y.-J. Jiang, S.-Y. Zhang, Y.-Q. Fan, and Y.-J. Pan Tetrahedron Lett. 49 2008 4652
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.