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Volumn 64, Issue 21, 1999, Pages 7890-7901

Rational synthesis of trans-substituted porphyrin building blocks containing one sulfur or oxygen atom in place of nitrogen at a designated site

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN; OXYGEN; PORPHYRIN DERIVATIVE; SULFUR;

EID: 0032697278     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909305     Document Type: Article
Times cited : (112)

References (49)
  • 29
    • 0007358814 scopus 로고    scopus 로고
    • Michl, J., Ed.; NATO ASI Series C: Mathematical and Physical Sciences, Kluwer Academic Publishers: Dordrecht
    • Lindsey, J. S. In Modular Chemistry; Michl, J., Ed.; NATO ASI Series C: Mathematical and Physical Sciences, Vol. 499; Kluwer Academic Publishers: Dordrecht, 1997; pp 517-528.
    • (1997) Modular Chemistry , vol.499 , pp. 517-528
    • Lindsey, J.S.1
  • 35
    • 33847508513 scopus 로고    scopus 로고
    • Use of TFA as an alternate catalyst was briefly examined. Reaction of 11 in pyrrole (64 mol equiv) catalyzed by TFA ( 1 mol equiv) also gave furylpyrromethane 15 in excellent yield (88%). However, reaction of 12 using TFA (1 mol equiv) gave 18 in 28% yield. More TFA (4 mol equiv) increased the yield to 76%.
    • Use of TFA as an alternate catalyst was briefly examined. Reaction of 11 in pyrrole (64 mol equiv) catalyzed by TFA ( 1 mol equiv) also gave furylpyrromethane 15 in excellent yield (88%). However, reaction of 12 using TFA (1 mol equiv) gave 18 in 28% yield. More TFA (4 mol equiv) increased the yield to 76%.
  • 36
    • 33847507657 scopus 로고    scopus 로고
    • The furyl/thienylpyrromethane yields were insensitive to the excess of pyrrole over the range studied (23-66 mol equiv).
    • The furyl/thienylpyrromethane yields were insensitive to the excess of pyrrole over the range studied (23-66 mol equiv).
  • 37
    • 33847513804 scopus 로고    scopus 로고
    • Greater than 5-fold excesses of ethylmagnesium bromide and p-toluoyl chloride did not significantly increase the ratio of diacyldipyrromethane to monoacyldipyrromethane.
    • Greater than 5-fold excesses of ethylmagnesium bromide and p-toluoyl chloride did not significantly increase the ratio of diacyldipyrromethane to monoacyldipyrromethane.
  • 38
    • 33744602342 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy of isolated samples. (Original NMR spectra of these byproducts are provided in the Supporting Information.)
  • 41
    • 33744633666 scopus 로고    scopus 로고
    • note
    • 3 in order to prevent rapid acidcatalyzed decomposition of the diols.
  • 42
    • 33744649230 scopus 로고    scopus 로고
    • note
    • The signal-to-noise ratio of LD-MS typically exceeded 100:1. The MS method cannot exclude the selective scrambling yielding only the cis-porphyrin or the movement of the heteroatom within the core. However, rearrangement processes leading to such isomers would be expected to form a distribution of porphyrin products, including those of other masses. See ref 23.
  • 43
    • 33744674995 scopus 로고    scopus 로고
    • note
    • 4Cl.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.