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Volumn 72, Issue 26, 2007, Pages 10254-10257

Synthesis of polysubstituted cyclopentenones via [4+1] reactions of TIPS-vinylketenes

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CYCLIC VOLTAMMETRY; REACTION RATES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 37549031765     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702109e     Document Type: Article
Times cited : (18)

References (51)
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    • For reviews, see: a
    • For reviews, see: (a) Tius, M. A. Eur. J. Org. Chem. 2005, 2193.
    • (2005) Eur. J. Org. Chem , pp. 2193
    • Tius, M.A.1
  • 17
    • 0003828015 scopus 로고
    • For a review, see: b, Wiley: New York
    • For a review, see: (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995.
    • (1995) Ketenes
    • Tidwell, T.T.1
  • 18
    • 47249106330 scopus 로고    scopus 로고
    • Danheiser, R. L, Ed, Thieme: New York, Chapter 2, Houben-Weyl
    • (c) George, D. M.; Danheiser, R. L. Science of Synthesis; Danheiser, R. L., Ed.; Thieme: New York, 2006; Vol. 23, Chapter 2, Houben-Weyl.
    • (2006) Science of Synthesis , vol.23
    • George, D.M.1    Danheiser, R.L.2
  • 19
    • 0026344585 scopus 로고    scopus 로고
    • Rigby's pioneering work revealed that isocynides could undergo [4+1] reaction with vinyl isocyanates to form nitrogen heterocycles. See: Rigby, J. H.; Qabar, M. J. Am. Chem. Soc. 1991, 113, 8975.
    • (a) Rigby's pioneering work revealed that isocynides could undergo [4+1] reaction with vinyl isocyanates to form nitrogen heterocycles. See: Rigby, J. H.; Qabar, M. J. Am. Chem. Soc. 1991, 113, 8975.
  • 32
    • 37549043863 scopus 로고    scopus 로고
    • In the preparation of 1k, product with Cr(CO)3 complexed C3 naphthyl ring was not found probably because Cr(CO)3 was easily decomposed in refluxing benzene. In the case of 1l, the TIPS-vinylketene with Cr(CO)3 complexed C3 naphthyl ring was found to be very unstable as expected, so 1l was formed by photolysis of crude product
    • 3 complexed C3 naphthyl ring was found to be very unstable as expected, so 1l was formed by photolysis of crude product.
  • 34
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    • For a review, see
    • (b) For a review, see: Braun, M. Angew. Chem., Int. Ed. 1998, 37, 430.
    • (1998) Angew. Chem., Int. Ed , vol.37 , pp. 430
    • Braun, M.1
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    • New Synthetic Pathways from Cyclobutanones
    • Halton, B, Ed, JAI Press: Greenwich, CT
    • (b) Lee-Ruff, E. New Synthetic Pathways from Cyclobutanones. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 1, pp 167-213.
    • (1991) Advances in Strain in Organic Chemistry , vol.1 , pp. 167-213
    • Lee-Ruff, E.1
  • 50
    • 37549065461 scopus 로고    scopus 로고
    • 2, with the plus charge on carbon. An sp geometry may also be reasonable, as this would maintain conjugation of all the electrons on nitrogen, with plus charge on N.
    • 2, with the plus charge on carbon. An sp geometry may also be reasonable, as this would maintain conjugation of all the electrons on nitrogen, with plus charge on N.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.