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Volumn 70, Issue 7, 2005, Pages 2771-2777

Synthesis of methyl carbamates from primary aliphatic amines and dimethyl carbonate in supercritical CO2: Effects of pressure and cosolvents and chemoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC COMPOUNDS; ORGANIC SOLVENTS; PRESSURE EFFECTS; REACTION KINETICS; STEREOCHEMISTRY; SUPERCRITICAL FLUIDS; SYNTHESIS (CHEMICAL);

EID: 17144418485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0477796     Document Type: Article
Times cited : (41)

References (47)
  • 9
    • 0003348455 scopus 로고    scopus 로고
    • Anastas, P., P. Williamson, P., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, Chapter 6
    • (b) Rivetti, F.; Romano, U.; Delledonne, D. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P., P. Williamson, P., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 6, pp 70-90.
    • (1996) Green Chemistry: Designing Chemistry for the Environment , pp. 70-90
    • Rivetti, F.1    Romano, U.2    Delledonne, D.3
  • 25
    • 17144421750 scopus 로고    scopus 로고
    • note
    • This was confirmed by the visual observation of the reaction mixture through sapphire windows placed on top and bottom covers of the autoclave.
  • 27
    • 17144373515 scopus 로고    scopus 로고
    • note
    • It should also be noted that if the N-methylation of reagents would not take place (especially at the lower pressure), the difference in conversions at 5 and 40 bar would probably be even more remarkable.
  • 28
    • 17144394623 scopus 로고    scopus 로고
    • note
    • 2 in the carbamate synthesis.
  • 37
    • 17144365631 scopus 로고    scopus 로고
    • note
    • The selectivity for compounds 5a is calculated as 5a/(3a + 4a + 5a + 6a + 7a). For reactions of Figure 2A, the amounts of compound 7a were of 0.5%, 4%, and 7% at 6, 107 and 150 bar, respectively; compound 6a was detected (1%) only at 6 bar.
  • 42
    • 17144399046 scopus 로고    scopus 로고
    • note
    • DMSO is highly hygroscopic and the presence of water may account for the observed behavior.
  • 43
    • 17144384233 scopus 로고    scopus 로고
    • note
    • The case of DMF cannot be considered because of the concomitant formation of product 8a.
  • 44
    • 0003055647 scopus 로고    scopus 로고
    • Wiley-VCH: Chapter 1
    • 2 (∈ = 1.3, fairly independent of pressure up to 300 bar. See: Chemical Synthesis Using Supercritical Fluids; Jessop, P. G., Leitner, W., Eds.; Wiley-VCH: 1999; Chapter 1, pp 1-36) and even greater than that of DMC (∈ = 3.1).
    • (1999) Chemical Synthesis Using Supercritical Fluids , pp. 1-36
    • Jessop, P.G.1    Leitner, W.2
  • 46
    • 0026644849 scopus 로고
    • 2Me, the selective formation of the carbamate 5f was reported, though a very low temperature (-78°C) was necessary. Prugh, J. D.; Birchenough, L. A.; Egbertson, M. S. Synth. Commun. 1992, 16, 2357-60.
    • (1992) Synth. Commun. , vol.16 , pp. 2357-2360
    • Prugh, J.D.1    Birchenough, L.A.2    Egbertson, M.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.