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Volumn , Issue 2, 2007, Pages 241-248

Investigating direct alkynylation at the bridgehead of bicyclic cages using silver(I) acetylides

Author keywords

Adamantanes; Alkynylation; Bicyclic cages; Bridgehead reactions; Carbon carbon bond formation; Carborate anions; Silver(I) acetylides

Indexed keywords


EID: 33846552604     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600701     Document Type: Article
Times cited : (26)

References (70)
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    • G. Capozzi, R. Ottaná, G. Romeo, F. Marcuzzi, Gazz. Chim. Ital. 1985, 115, 311-314 and references cited therein;
    • a) G. Capozzi, R. Ottaná, G. Romeo, F. Marcuzzi, Gazz. Chim. Ital. 1985, 115, 311-314 and references cited therein;
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    • 0032548045 scopus 로고    scopus 로고
    • J. Xiang, P. L. Fuchs, Tetrahedron Lett. 1998, 39, 8597-8600 and references cited therein;
    • b) J. Xiang, P. L. Fuchs, Tetrahedron Lett. 1998, 39, 8597-8600 and references cited therein;
  • 11
    • 17444368099 scopus 로고    scopus 로고
    • Part of this work has already appeared in communication form, see
    • Part of this work has already appeared in communication form, see R. H. Pouwer, C. M. Williams, A. L. Raine, J. B. Harper, Org. Lett. 2005, 7, 1323-1325.
    • (2005) Org. Lett , vol.7 , pp. 1323-1325
    • Pouwer, R.H.1    Williams, C.M.2    Raine, A.L.3    Harper, J.B.4
  • 14
  • 40
    • 0025218608 scopus 로고    scopus 로고
    • Silver(I) acetylides are known to undergo 1,4-conjugate addition, see T. Kauffmann, A. Hülsdünker, D. Menges, H. Nienaber, S. Robbe, D. Scherler, J. Schrickel, D. Wingbermühle, Tetrahedron Lett. 1990, 31, 1553.
    • Silver(I) acetylides are known to undergo 1,4-conjugate addition, see T. Kauffmann, A. Hülsdünker, D. Menges, H. Nienaber, S. Robbe, D. Scherler, J. Schrickel, D. Wingbermühle, Tetrahedron Lett. 1990, 31, 1553.
  • 59
    • 33846522563 scopus 로고    scopus 로고
    • Mechanistic studies were evaluated using GC/MS on the reaction of silver(I) phenylacetylide (50 mg, 2 equiv.) and 1-iodoadamantane (30 mg, 1 equiv.) in N-methylmorpholine (1.0 mL) at 116°C under argon for 16 h.
    • Mechanistic studies were evaluated using GC/MS on the reaction of silver(I) phenylacetylide (50 mg, 2 equiv.) and 1-iodoadamantane (30 mg, 1 equiv.) in N-methylmorpholine (1.0 mL) at 116°C under argon for 16 h.


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