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Volumn 43, Issue 48, 2002, Pages 8669-8672

Novel intramolecular photocyclization of tris(2-benzo[b]thienyl)methyl alcohol

Author keywords

trimerization; Benzo b thiophene ring; Di methane rearrangement; Photocyclization; Tropone derivative

Indexed keywords

ACETONITRILE; ALCOHOL DERIVATIVE; BENZOTHIOPHENE; CYCLOPENTANONE DERIVATIVE; METHANE; TRIS(2 BENZO[B]THIENYL)METHYL ALCOHOL; TROPONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037175486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02161-5     Document Type: Article
Times cited : (13)

References (22)
  • 5
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    • 3: C, 70.09; H, 3.74; S, 22.43. Found: C, 70.13; H, 3.98, S, 22.04.
    • 3: C, 70.09; H, 3.74; S, 22.43. Found: C, 70.13; H, 3.98, S, 22.04.
  • 6
    • 0011188451 scopus 로고    scopus 로고
    • 3: C, 70.75; H, 2.83, S, 22.64. Found: C, 70.56; H, 2.76; S, 22.44.
    • 3: C, 70.75; H, 2.83, S, 22.64. Found: C, 70.56; H, 2.76; S, 22.44.
  • 7
    • 0011245480 scopus 로고    scopus 로고
    • NOE-enhancement was not observed between the methine protons in 3- and 4-positions of the cyclopentanone ring.
    • NOE-enhancement was not observed between the methine protons in 3- and 4-positions of the cyclopentanone ring.
  • 8
    • 0011189846 scopus 로고    scopus 로고
    • 13C NMR: the chemical shift of 179.5 ppm corresponds to that of the carbonyl carbons in esters rather than cyclic ketones.
    • 13C NMR: the chemical shift of 179.5 ppm corresponds to that of the carbonyl carbons in esters rather than cyclic ketones.
  • 9
    • 0011255316 scopus 로고    scopus 로고
    • note
    • Besides 3a, there are three other possibilities, A, B and C, for the pattern of benzo[b]thiophene-fusion. However, none of them can rationalize the spectral characteristics. For A and B the chemical shifts of two face-to-face aromatic protons should occur in lower field than that observed because of their remarkable proximity. Furthermore, the NOE measurements of 3a gave no evidence for the presence of closely-neighboring protons. For C two protons facing the carbonyl group should exhibit almost the same chemical shift because of the nearly equivalent environment.
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    • -1.
    • -1.
  • 11
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    • A possible intermediate, a bicyclo[2.1.0]pentane derivative, was not detected in the photoreaction mixture.
    • A possible intermediate, a bicyclo[2.1.0]pentane derivative, was not detected in the photoreaction mixture.
  • 12
    • 0024987611 scopus 로고    scopus 로고
    • Shi, M.; Okamoto, Y.; Takamuku, S. Bull. Chem. Soc. Jpn. 1990, 63, 453 and 2731.
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    • D.N. Neckers, G. von Bunau, & W.S. Jenks. NewYork: John Wiley
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    • (2001) Advances in Photochemistry , vol.26 , pp. 1
    • Jarikov, V.V.1    Neckers, D.C.2
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    • V. Ramamurthy, & K.S. Schanze. New York: Marcel Dekker
    • Boyd M.K. Ramamurthy V., Schanze K.S., Organic Photochemistry. 1997;147 Marcel Dekker, New York.
    • (1997) Organic Photochemistry , pp. 147
    • Boyd, M.K.1
  • 22
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    • max (ε) 387 (2100), 402 (2500) nm.
    • max (ε) 387 (2100), 402 (2500) nm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.