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Volumn 2, Issue 11, 2000, Pages 1497-1500

Intramolecular [4 + 2] Cycloaddition Reactions of Diarylacetylenes: Synthesis of Benzo[b]fluorene Derivatives via Cyclic Allenes

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EID: 0000402121     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991391t     Document Type: Article
Times cited : (94)

References (34)
  • 2
    • 0040715906 scopus 로고    scopus 로고
    • Thermolysis of 2a at 110°C for 10 days to give the isomeric benzo-[b]fluorenols 4a (44%) and 5a (13%) had been previously described: Schmittel, M.; Strittmatter, M.; Schenk, W. A.; Hagel, M. Z. Naturforsch 1998, 53b, 1015-1020.
    • (1998) Z. Naturforsch , vol.53 B , pp. 1015-1020
    • Schmittel, M.1    Strittmatter, M.2    Schenk, W.A.3    Hagel, M.4
  • 18
    • 0442330934 scopus 로고    scopus 로고
    • note
    • Benzo[b]fluorenones 4b and 5b had been obtained previously as byproducts when studying thermolysis of 2a at 110°C. See ref 2.
  • 19
    • 0442330933 scopus 로고    scopus 로고
    • note
    • See Supporting Information for experimental details.
  • 21
    • 33748240634 scopus 로고
    • For a theoretical study of 1,2,4-cyclohexatriene, a conjugated cyclic allene, see: Janoschek, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 476-478.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 476-478
    • Janoschek, R.1
  • 26
    • 0033595573 scopus 로고    scopus 로고
    • and references therein
    • Although pure functionals have recently been used for description of species with biradical character, we achieved better results using hybrid functionals. Schreiner, P. R.; Prall, M. J. Am. Chem. Soc. 1999, 121, 8615-8627 and references therein.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8615-8627
    • Schreiner, P.R.1    Prall, M.2
  • 29
    • 0442299745 scopus 로고    scopus 로고
    • note
    • The combination of these two factors was inferred using MCSCF and B3LYP calculations for the models (Z)-4-heptene-1,6-diyn-3-one and (Z)-3-heptene-1,6-diyne. Results to be published elsewhere.
  • 32
    • 0442299744 scopus 로고    scopus 로고
    • Results to be published elsewhere
    • Results to be published elsewhere.
  • 33
    • 0442283881 scopus 로고    scopus 로고
    • note
    • This hypothesis had been suggested previously by Danheiser et al. See ref 5a.
  • 34
    • 0442283880 scopus 로고    scopus 로고
    • note
    • Increased yield in the presence of a proton source (ArOH) has been observed previously in intramolecular [4 + 2] cycloadditions. See ref 5a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.