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Volumn 52, Issue 4, 2011, Pages 483-487

Zinc chloride homogeneous catalysis in the tritylation of hydroxyl- and amide-bearing molecules

Author keywords

Amide group tritylation; Catalyzed trityl transfer; O Tritylation; Trityl acetate; Zinc chloride

Indexed keywords

ACETONITRILE; AMIDE; BENZYL ALCOHOL DERIVATIVE; ETHER DERIVATIVE; HYDROXYL GROUP; TRITYL DERIVATIVE; ZINC CHLORIDE;

EID: 78650520314     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.095     Document Type: Article
Times cited : (9)

References (52)
  • 2
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    • 71849097295 scopus 로고    scopus 로고
    • WO 2007009944 A1, 2007, 20070125
    • Maltese, M. PCT Int. Appl. WO 2007009944 A1, 2007, 20070125.
    • PCT Int. Appl.
    • Maltese, M.1
  • 29
    • 0001345095 scopus 로고    scopus 로고
    • 3 have been employed in the oxidation of ditrialkylsilyl enol ethers (see Jung, M. E.; Pan, Y.-G. J. Org. Chem. 1977, 42, 3961-3963)
    • 3 have been employed in the oxidation of ditrialkylsilyl enol ethers (see Jung, M. E.; Pan, Y.-G. J. Org. Chem. 1977, 42, 3961-3963).
  • 36
    • 78650520885 scopus 로고    scopus 로고
    • note
    • The tritylating reagents have been prepared by mixing anhydrous formic or acetic acid with equimolar quantities of trityl chloride and triethylamine in acetonitrile or DCM at room temperature, then isolated and purified as follows: 5 min after the introduction of formic or acetic acid in the reagent mixture, the solvent was evaporated under vacuum and the residue extracted with ether. The suspension was filtered off and the filtrate evaporated under vacuum. In general, the residue was used as the reagent without further purification. Crystallization of the trityl esters 1b and 2b for analytical purposes has been obtained by addition of n-hexane to the residue. The use of 1b or 2b in the presence of triethylammonium chloride obtained as secondary product in their preparations has always given lower yields of the desired product.
  • 41
    • 33947481827 scopus 로고    scopus 로고
    • note
    • 3 as the catalyst. However, the authors report for this compound a mp 96-98 °C instead of 152-53 °C reported in the literature for 9b: (a) Wang, C. H. J. Org. Chem. 1963, 28, 2914-2915; (b) Klinger, H.; Lonnes, C. Chem. Ber. 1896, 29, 2159-2167. We have synthesized the dibenzhydryl ether and found that the signal for our 9b at 5.57 δ corresponds to 1 proton, while that at 5.42 δ in the spectrum of the symmetric ether (corresponding to 5.36 δ and reported as (s, 1H) in the cited paper) corresponds to 2 protons.
  • 48
    • 78650521937 scopus 로고    scopus 로고
    • Patent EPO394194 and references therein
    • Patent EPO394194 and references therein.
  • 49
    • 78650520570 scopus 로고    scopus 로고
    • Despite amides are bi-dentate substrates and both O- and N-tritylation should occur (as effectively observed in the case of pyridones, see Ref. 27), we have obtained only the N-trityl derivatives
    • Despite amides are bi-dentate substrates and both O- and N-tritylation should occur (as effectively observed in the case of pyridones, see Ref. 27), we have obtained only the N-trityl derivatives.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.