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Volumn , Issue 2, 2004, Pages 377-379

Homocoupling of 1-Alkynyl Tosylamides

Author keywords

Alkyne homocoupling; Butadiynes; Copper catalyzed dimerization; Ynamides

Indexed keywords

AMIDE; COPPER; TOLUENESULFONIC ACID DERIVATIVE;

EID: 1242273631     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-45010     Document Type: Article
Times cited : (43)

References (36)
  • 3
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    • Marcel Dekker: New York, Chap. 12
    • (c) Viehe, H. G. Chemistry of Acetylenes: Marcel Dekker: New York, 1969, Chap. 12, 861-912.
    • (1969) Chemistry of Acetylenes , pp. 861-912
    • Viehe, H.G.1
  • 5
    • 0000868359 scopus 로고
    • Kropf, H.; Schaumann. E., Eds.; Georg Thieme Verlag: Stuttgart
    • (e) Himbert, G. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann. E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3267-3443.
    • (1993) Houben-Weyl, Methoden der Organischen Chemie , pp. 3267-3443
    • Himbert, G.1
  • 24
    • 1242347921 scopus 로고
    • As well as finding no precedent for the Glaser reaction of ynamides, we found only few ynamines dimerization: (a) Ficini, J.; Barbara, C.; d'Angelo, J. ; Duréault, A. Bull. Soc. Chim. Fr. 1974, 1535. (b) Mayerle, J. J.; Flandera, M. A. Acta Crystallogr., Section B 1978, 34, 1374; no experimental details are given.
    • (1974) Bull. Soc. Chim. Fr. , pp. 1535
    • Ficini, J.1    Barbara, C.2    D'Angelo, J.3    Duréault, A.4
  • 25
    • 0000706251 scopus 로고
    • no experimental details are given
    • As well as finding no precedent for the Glaser reaction of ynamides, we found only few ynamines dimerization: (a) Ficini, J.; Barbara, C.; d'Angelo, J. ; Duréault, A. Bull. Soc. Chim. Fr. 1974, 1535. (b) Mayerle, J. J.; Flandera, M. A. Acta Crystallogr., Section B 1978, 34, 1374; no experimental details are given.
    • (1978) Acta Crystallogr., Section B , vol.34 , pp. 1374
    • Mayerle, J.J.1    Flandera, M.A.2
  • 27
    • 1242280606 scopus 로고    scopus 로고
    • note
    • Trimethylsilyl derivatives are interesting substrates that can also be prepared in a single step from the corresponding N-alkyltosylamides by reaction with hypervalent iodonium reagents, see: ref. 5b
  • 29
    • 85085719087 scopus 로고    scopus 로고
    • note
    • 3N gave a slow dimerization process.
  • 31
    • 1242280607 scopus 로고    scopus 로고
    • note
    • 2: C, 66.65; H, 4.47; N, 5.18; S, 11.86. Found: C, 66.21; H, 4.21; N, 5.27; S, 11.67.
  • 32
    • 85085719419 scopus 로고    scopus 로고
    • note
    • 3 before mixing with HCl (5%) or NaOH (10%).
  • 34
    • 0002358128 scopus 로고    scopus 로고
    • Ynamide 2b reacted much faster (in 0.5 h) than the non-nitrogenated acetylenes used by Mori and coworkers, which took 6-12 h. See: (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039. (b) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Mori, A. ; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
    • (1997) Chem. Commun. , pp. 1039
    • Ikegashira, K.1    Nishihara, Y.2    Hirabayashi, K.3    Mori, A.4    Hiyama, T.5
  • 35
    • 0034708636 scopus 로고    scopus 로고
    • Ynamide 2b reacted much faster (in 0.5 h) than the non-nitrogenated acetylenes used by Mori and coworkers, which took 6-12 h. See: (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039. (b) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Mori, A. ; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
    • (2000) J. Org. Chem. , vol.65 , pp. 1780
    • Nishihara, Y.1    Ikegashira, K.2    Hirabayashi, K.3    Ando, J.-I.4    Mori, A.5    Hiyama, T.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.