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Volumn 69, Issue 14, 2004, Pages 4845-4848

Selenoimidoylation of alcohols with selenium and isocyanides and its application to the synthesis of selenium-containing heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; CHEMICAL BONDS; REACTION KINETICS; SELENIUM; SYNTHESIS (CHEMICAL);

EID: 3042784663     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0496704     Document Type: Article
Times cited : (34)

References (48)
  • 13
    • 4244214556 scopus 로고
    • (c) Burutus, M.; Mollier, Y.; Stavaux, M. Nouv. J. Chim. 1986, 10, 51; Chem. Abstr. 1987, 106, 195792.
    • (1987) Chem. Abstr. , vol.106 , pp. 195792
  • 22
    • 85166601322 scopus 로고    scopus 로고
    • (j) Blum, T.; Ermwrt, J.; Coenen, H. H. J. Labelled Comp. Radiopharm. 2001, 44, 587; Chem. Abstr. 2001, 135, 344558.
    • (2001) Chem. Abstr. , vol.135 , pp. 344558
  • 38
    • 3042848300 scopus 로고    scopus 로고
    • note
    • Selenocarbonimidate 4b was also obtained in 72% yield when the reaction was carried out under conditions similar to those shown in eqs 1 and 2 by starting with MeOLi.
  • 39
    • 3042770309 scopus 로고    scopus 로고
    • note
    • 1H NMR of 4b showed a set of peaks assignable to a single isomer. However, we could not determine the stereochemistry of the carbon-nitrogen double bond because a nuclear Overhauser effect was not observed when we irradiated methyl protons of 2,6-xylyl group in 4b.
  • 45
    • 3042727789 scopus 로고    scopus 로고
    • note
    • The product selectivity observed is due to higher nucleophilicity of the selenium atom. In fact, the product ratio was almost the same when the reaction time was shortened to 1 h. Isolated 10e and 11e were not interconverted under similar reaction conditions.
  • 46
    • 0035951572 scopus 로고    scopus 로고
    • 9b,d were prepared by modified reactions of the general procedure for synthesis of aryl alkynes reported in the following paper; Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412.
    • (2001) J. Org. Chem. , vol.66 , pp. 412
    • Roesch, K.R.1    Larock, R.C.2
  • 47
    • 0000817870 scopus 로고
    • Conversion of 2,6-xylidine to 2,6-xylyl formamide, see: Krishnamurthy, S. Tetrahedron Lett. 1982, 23, 3315. Dehydration of 2,6-xylyl formamide to 2,6-xylyl isocyanide, see: Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1985, 400.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3315
    • Krishnamurthy, S.1
  • 48
    • 85005647840 scopus 로고
    • Conversion of 2,6-xylidine to 2,6-xylyl formamide, see: Krishnamurthy, S. Tetrahedron Lett. 1982, 23, 3315. Dehydration of 2,6-xylyl formamide to 2,6-xylyl isocyanide, see: Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1985, 400.
    • (1985) Synthesis , pp. 400
    • Obrecht, R.1    Herrmann, R.2    Ugi, I.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.