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Volumn 70, Issue 9, 2005, Pages 3727-3729

A rapid synthesis of 2-aryl-5-substituted-2,3-dihydrobenzofurans

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHEMICAL REACTIONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TOLUENE;

EID: 17744369288     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0500941     Document Type: Article
Times cited : (41)

References (66)
  • 54
    • 0036261439 scopus 로고    scopus 로고
    • 2,4,6-Trinitrotoluene (TNT) has been reported to undergo a stepwise conversion to 2,3-dihydrobenzofurans, see: Rozhkov, V. V.; Kuvshinov, A. M.; Shevelev, S. A. Synth. Commun. 2002, 32, 1465.
    • (2002) Synth. Commun. , vol.32 , pp. 1465
    • Rozhkov, V.V.1    Kuvshinov, A.M.2    Shevelev, S.A.3
  • 55
    • 17744399480 scopus 로고    scopus 로고
    • note
    • Reaction of 11 under the reaction conditions (1.5 equiv of TBAF, THF, reflux) in the absence of any aldehyde gave nearly quantitative conversion to 3-methyl-4-nitrobenzoic acid.
  • 57
    • 2142694795 scopus 로고
    • For the reaction of nitrotoluenes with aldehydes in the presence of NaOMe/DMSO, see: (a) Bakke, J. Acta Chem. Scand. 1967, 21, 1967.
    • (1967) Acta Chem. Scand. , vol.21 , pp. 1967
    • Bakke, J.1
  • 59
    • 0030908763 scopus 로고    scopus 로고
    • For the reaction of nitrotoluenes with aldehydes in the presence of NaOMe/DMF, see: (a) Rollins, S. B.; Williams, R. M. Tetrahedron Lett. 1997, 38, 4033.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4033
    • Rollins, S.B.1    Williams, R.M.2
  • 62
    • 0024362041 scopus 로고
    • For the reaction of a nitrotoluene with formaldehyde in the presence of KOH/DMSO, see: Yasuda, N.; Williams, R. M. Tetrahedron Lett. 1989, 30, 3397.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3397
    • Yasuda, N.1    Williams, R.M.2
  • 64
    • 17744380383 scopus 로고    scopus 로고
    • note
    • Unidentified reaction byproducts, most likely arrising from deprotonation of the methyl sulfone, account for the mass balance.
  • 66
    • 17744381930 scopus 로고    scopus 로고
    • note
    • Significant amounts of starting materials, in addition to some decomposition, account for the mass balance.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.