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Volumn , Issue 19, 2005, Pages 3355-3361

Conversion of alkyl halides into alcohols via formyloxylation reaction with DMF catalyzed by silver salts

Author keywords

Alcohols; Alkyl halides; Catalysis; Eliminations; Nucleophilic substitutions

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; ESTERS; HALIDE MINERALS; HYDROLYSIS; SILVER COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 29044446411     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918453     Document Type: Article
Times cited : (15)

References (46)
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    • Barton, D. H. R.; Ollis, W. D.; Sutherland, I. O., Eds.; Pergamon Press: Oxford
    • (a) Wilkinson, S. G. In Alcohols, Phenols, Ethers and Related Compounds, In Comprehensive Organic Chemistry, The Synthesis and Reactions of Organic Compounds, Vol. 1; Barton, D. H. R.; Ollis, W. D.; Sutherland, I. O., Eds.; Pergamon Press: Oxford, 1979, 595.
    • (1979) Comprehensive Organic Chemistry, the Synthesis and Reactions of Organic Compounds , vol.1 , pp. 595
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  • 2
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    • Synthesis of Alcohols and Ethers
    • Trost, B. N.; Fleming, I, Eds.; Pergamon Press: Oxford
    • (b) Mitsunobo, O. In Synthesis of Alcohols and Ethers, In Comprehensive Organic Synthesis, Vol. 6; Trost, B. N.; Fleming, I, Eds.; Pergamon Press: Oxford, 1993, 2.
    • (1993) Comprehensive Organic Synthesis , vol.6 , pp. 2
    • Mitsunobo, O.1
  • 3
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    • Synthesis of Esters
    • Trost, B. N.; Fleming, I, Eds.; Pergamon Press: Oxford
    • (c) Mulzer, J. In Synthesis of Esters, In Comprehensive Organic Synthesis, Vol. 6; Trost, B. N.; Fleming, I, Eds.; Pergamon Press: Oxford, 1993, 335.
    • (1993) Comprehensive Organic Synthesis , vol.6 , pp. 335
    • Mulzer, J.1
  • 12
    • 0037454656 scopus 로고    scopus 로고
    • For recent examples of C-X to C-O Ag-assisted conversions, see, in addition to the above mentioned bis(tributyltin)oxide/Ag(I)/DMF hydrolysis of primary halides: (a) Toyonari, I.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. Tetrahedron 2003, 59, 525.
    • (2003) Tetrahedron , vol.59 , pp. 525
    • Toyonari, I.1    Tokuyasu, T.2    Masuyama, A.3    Nojima, M.4    McCullough, K.J.5
  • 23
    • 0000100983 scopus 로고
    • For detailed mechanistic studies on the thermal alkylation reaction of formamides and other amides with alkyl halides, see: (a) Brace, N. O. J. Org. Chem. 1993, 58, 1804.
    • (1993) J. Org. Chem. , vol.58 , pp. 1804
    • Brace, N.O.1
  • 24
    • 0029821222 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Brace, N. O. J. Org. Chem. 1996, 61, 6504; and references cited therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 6504
    • Brace, N.O.1
  • 25
    • 29044432469 scopus 로고    scopus 로고
    • Ger. Offen. DE No 2,318.941, 1973; Asahi Glass Co., Ltd.
    • Hayashi, T.; Matsuo, M. Ger. Offen. DE No 2,318.941, 1973; Asahi Glass Co., Ltd.
    • Hayashi, T.1    Matsuo, M.2
  • 28
    • 29044448924 scopus 로고
    • Chem. Abstr. 1966, 64, 35341.
    • (1966) Chem. Abstr. , vol.64 , pp. 35341
  • 30
    • 0034727319 scopus 로고    scopus 로고
    • Several C-X (X = Br, I) to COCHO transformations by DMF/Ag(I) salt have been described in the literature, which were considered as unexpected reactions and generally in the context of cationic rearrangements promoted by Ag(I) in DMF, see: (a) Chang, R.-K.; Kim, K. Tetrahedron Lett. 2000, 41, 8499.
    • (2000) Tetrahedron Lett , vol.41 , pp. 8499
    • Chang, R.-K.1    Kim, K.2
  • 38
    • 29044440977 scopus 로고    scopus 로고
    • note
    • 3-2).
  • 40
    • 29044437474 scopus 로고    scopus 로고
    • note
    • 3 (up to 25%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.