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Volumn , Issue 28, 2007, Pages 4642-4645

The ritter reaction under truly catalytic bronsted acid conditions

Author keywords

Alcohols; Amides; Bronsted acids; Homogeneous catalysis; Ritter reaction

Indexed keywords


EID: 35348834322     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700562     Document Type: Article
Times cited : (91)

References (44)
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    • For intramolecular applicatons of the Ritter reaction to alcohol derivatives, see; a
    • For intramolecular applicatons of the Ritter reaction to alcohol derivatives, see; a) K. V. Emelen, T. De Wit, G. J. Hoornaert, F. Compernolle, Org. Lett. 2000, 2, 3083-3086;
    • (2000) Org. Lett , vol.2 , pp. 3083-3086
    • Emelen, K.V.1    De Wit, T.2    Hoornaert, G.J.3    Compernolle, F.4
  • 5
    • 0008267756 scopus 로고    scopus 로고
    • Moderate yields are obtained with primary and secondary benzylic alcohols, see for instance: a C. L. Parris, R. M. Christenson, J. Org. Chem. 1960, 25, 331-334;
    • Moderate yields are obtained with primary and secondary benzylic alcohols, see for instance: a) C. L. Parris, R. M. Christenson, J. Org. Chem. 1960, 25, 331-334;
  • 22
    • 33645909561 scopus 로고    scopus 로고
    • For the use of a borate complex as catalyst, see
    • e) For the use of a borate complex as catalyst, see: T. Maki, K. Ishihara, H. Yamamoto, Org. Lett. 2006, 8, 1431-1434.
    • (2006) Org. Lett , vol.8 , pp. 1431-1434
    • Maki, T.1    Ishihara, K.2    Yamamoto, H.3
  • 31
    • 33750037029 scopus 로고    scopus 로고
    • DNBSA has been reported as an efficient Bransted acid catalyst for the Hosomi-Sakurai reaction of acetals, see: D. Kampen, B. List, Synlett 2006, 2589-2592
    • DNBSA has been reported as an efficient Bransted acid catalyst for the Hosomi-Sakurai reaction of acetals, see: D. Kampen, B. List, Synlett 2006, 2589-2592.
  • 32
    • 35348813140 scopus 로고    scopus 로고
    • Disappointingly, a primary benzylic alcohol such as benzyl alcohol gave rise to low conversion (< 20%) under DNBSA catalysis.
    • Disappointingly, a primary benzylic alcohol such as benzyl alcohol gave rise to low conversion (< 20%) under DNBSA catalysis.
  • 36
    • 0034032537 scopus 로고    scopus 로고
    • Trifluoroacetic acid was used as solvent: M. Laurent, J. Marchand-Brynaert, Synthesis 2000, 667-672.
    • Trifluoroacetic acid was used as solvent: M. Laurent, J. Marchand-Brynaert, Synthesis 2000, 667-672.
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    • 0001631526 scopus 로고
    • a) Al: R. Wolovsky, N. Maoz, J. Org. Chem. 1973, 38, 4040-4044;
    • (1973) J. Org. Chem , vol.38 , pp. 4040-4044
    • Al, R.1
  • 38
    • 0037425133 scopus 로고    scopus 로고
    • Pd/In: T. Tsuchimoto, S. Kamiyama, R. Negoro, E. Shirakawa, Y. Kawakami, Chem. Commun. 2003, 852-853;
    • b) Pd/In: T. Tsuchimoto, S. Kamiyama, R. Negoro, E. Shirakawa, Y. Kawakami, Chem. Commun. 2003, 852-853;
  • 42
    • 35348912554 scopus 로고    scopus 로고
    • Under DNBSA catalysis at room temperature, a 2:1 mixture of 11a/12a was formed, showing the poor reproducibility on the ratio of 11/12.
    • Under DNBSA catalysis at room temperature, a 2:1 mixture of 11a/12a was formed, showing the poor reproducibility on the ratio of 11/12.
  • 43
    • 35348874854 scopus 로고    scopus 로고
    • We have also checked the reaction by using other nitriles different from acetonitrile. For example, positive results were obtained in the reaction of 1-phenylethanol (1a) with benzonitrile. Details on this work will be published at due time
    • We have also checked the reaction by using other nitriles different from acetonitrile. For example, positive results were obtained in the reaction of 1-phenylethanol (1a) with benzonitrile. Details on this work will be published at due time.
  • 44
    • 35348921761 scopus 로고    scopus 로고
    • We used 2,4-dinitrobenzenesulfonic acid hydrate (Aldrich, 556971, Its elemental analysis gave the molecular formula (NO2)2C 6H3SO3H·2.5H2O
    • 2O.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.