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Volumn 118, Issue 32, 1996, Pages 7634-7635

Ynolates from the reaction of lithiosilyldiazomethane with carbon monoxide. New ketenylation reactions

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; KETONE;

EID: 0029775846     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961229a     Document Type: Article
Times cited : (82)

References (46)
  • 17
    • 0001236226 scopus 로고
    • Silylethynolates by deprotonation of silylketenes. (a) Woodburgy, R. P.; Long, N. L.; Rathke, M. W. J. Org. Chem. 1978, 43, 376. (b) Kita, Y.; Tsutsumi, Y.; Kitagaki, S. Chem. Pharm. Bull. 1992, 42, 233. (c) By desilylation of bissilylketene, see: Ito, M.; Shirakawa, E.; Takaya, H. Abstract of the 70th Annual Meeting of the Chemical Society of Japan, Tokyo; March 1996, 2J392.
    • (1978) J. Org. Chem. , vol.43 , pp. 376
    • Woodburgy, R.P.1    Long, N.L.2    Rathke, M.W.3
  • 18
    • 9444295331 scopus 로고
    • Silylethynolates by deprotonation of silylketenes. (a) Woodburgy, R. P.; Long, N. L.; Rathke, M. W. J. Org. Chem. 1978, 43, 376. (b) Kita, Y.; Tsutsumi, Y.; Kitagaki, S. Chem. Pharm. Bull. 1992, 42, 233. (c) By desilylation of bissilylketene, see: Ito, M.; Shirakawa, E.; Takaya, H. Abstract of the 70th Annual Meeting of the Chemical Society of Japan, Tokyo; March 1996, 2J392.
    • (1992) Chem. Pharm. Bull. , vol.42 , pp. 233
    • Kita, Y.1    Tsutsumi, Y.2    Kitagaki, S.3
  • 19
    • 9444295330 scopus 로고    scopus 로고
    • Tokyo; March
    • Silylethynolates by deprotonation of silylketenes. (a) Woodburgy, R. P.; Long, N. L.; Rathke, M. W. J. Org. Chem. 1978, 43, 376. (b) Kita, Y.; Tsutsumi, Y.; Kitagaki, S. Chem. Pharm. Bull. 1992, 42, 233. (c) By desilylation of bissilylketene, see: Ito, M.; Shirakawa, E.; Takaya, H. Abstract of the 70th Annual Meeting of the Chemical Society of Japan, Tokyo; March 1996, 2J392.
    • (1996) Abstract of the 70th Annual Meeting of the Chemical Society of Japan
    • Ito, M.1    Shirakawa, E.2    Takaya, H.3
  • 30
    • 9444256946 scopus 로고    scopus 로고
    • note
    • Only scattered examples of ketenylation (a reaction that enables the nucleophilic introduction of a ketenyl unit into an organo molecule) have been known, see refs 2-6.
  • 31
    • 0002676988 scopus 로고
    • Shioiri, T.; Aoyama, T.; Mori, S. Org. Synth. 1990, 68, 1. A 2.0 M hexane solution of trimethylsilyldiazomethane is commercially available, purchased from Aldrich Chemical Co.
    • (1990) Org. Synth. , vol.68 , pp. 1
    • Shioiri, T.1    Aoyama, T.2    Mori, S.3
  • 32
    • 9444280127 scopus 로고    scopus 로고
    • note
    • All new compounds were characterized by NMR, IR, mass spectral data, and elemental analyses or high-resolution mass spectra. See the supporting information.
  • 34
    • 9444286413 scopus 로고
    • Nikolaeva, S. N.; Zolotareva, A. S.; Ponomarev, S. V.; Petrosyan, V. S. Izv. Akad. Nauk Ser. Khim. 1994, 911; Chem. Abstr. 1994, 122, 160751.
    • (1994) Chem. Abstr. , vol.122 , pp. 160751
  • 37
    • 84943963865 scopus 로고
    • Related reactions with transition metals have been reported: (a) Rüchardt, C.; Schrauzer, G. N. Chem. Ber. 1960, 93, 1840. (b) Deydier, E.; Menu, M.-J.; Dartiguenave, M.; Dartiguenave, Y. J. Organomet. Chem. 1993, 458, 255.
    • (1960) Chem. Ber. , vol.93 , pp. 1840
    • Rüchardt, C.1    Schrauzer, G.N.2
  • 39
    • 9444237374 scopus 로고    scopus 로고
    • note
    • 3Al, many products including β-lactones were obtained.
  • 40
    • 9444283774 scopus 로고    scopus 로고
    • note
    • With cis predominating although not fully established.
  • 44
    • 9444297294 scopus 로고    scopus 로고
    • note
    • 3Al mixture.
  • 45
    • 9444223281 scopus 로고    scopus 로고
    • note
    • A [2 + 4] or [2 + 2] cycloaddition cannot be ruled out in the reaction of 4 with α,β-unsaturated carbonyl compounds or imines.
  • 46
    • 9444256947 scopus 로고    scopus 로고
    • note
    • + from 4 without any assistance.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.