메뉴 건너뛰기




Volumn 2007, Issue 11, 2007, Pages 64-72

Approaches to benzo[b]thiophenes by gas-phase pyrolysis of methyl 2-(alkylthio)cinnamates

Author keywords

Benzothiophenes; Flash vacuum pyrolysis; Radicals; Thiocoumarins

Indexed keywords


EID: 33846320428     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.b06     Document Type: Article
Times cited : (8)

References (24)
  • 9
    • 85069248042 scopus 로고    scopus 로고
    • During the course of this work, it was discovered that the NMR spectra reported by Panetta and Rapoport9 from products obtained by reacting thiophenol with propiolic orthoesters and subsequent cyclisation, are those of thiochromones, not thiocoumarins as claimed. It follows that the reactions of thiophenols with propiolic orthoesters must take a different course from those of phenols,10 probably owing the much harder nature of the nucleophile in the latter case. Finally, the structures of the intermediate 2-mercaptocinnamates9 must be revised to corresponding β-(arylthio)acrylates, and available NMR data for the parent compound are also consistent with this interpretation.11 In the light of these structural revisions, it now becomes clear why the cyclisation step in the phenol case takes place in the presence of base,10 whereas the 'analogous' cyclisation of the thiophenol-derived intermediate is acid-catalysed,9
    • 12
  • 19
    • 85069251702 scopus 로고
    • Eur. Pat. Appl, EP 0350163;, 191969
    • Smith, S. A.; Ham, P.; Nash, D. J. Eur. Pat. Appl. 1990, EP 0350163; Chem. Abstr. 1990, 113, 191969.
    • (1990) Chem. Abstr , vol.113
    • Smith, S.A.1    Ham, P.2    Nash, D.J.3
  • 21
    • 5244227680 scopus 로고
    • Edition 1, Aldrich Chemical Company Inc, Milwaukee
    • 13C FTNMR Spectra Edition 1, Aldrich Chemical Company Inc.: Milwaukee, 1993; Vol. 3, 174A.
    • (1993) 13C FTNMR Spectra , vol.3
    • Pauchert, J.1    Behnke, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.