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Volumn 118, Issue 19, 1996, Pages 4719-4720

Photochemistry of thiarubrine A and other 1,2-dithiins: Formation of 2,6-dithiabicyclo[3.1.0]hex-3-enes

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; THIARUBRINE A;

EID: 0029895813     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960589v     Document Type: Article
Times cited : (44)

References (45)
  • 5
    • 0028090225 scopus 로고
    • and references therein.
    • (e) Koreeda, M.; Yang, W. J. Am. Chem. Soc. 1994, 116, 10793-10794 and references therein.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10793-10794
    • Koreeda, M.1    Yang, W.2
  • 13
    • 0012145180 scopus 로고
    • ACS Symposium Series 616; Heitz, J. R., Downum, K. R., Eds.; American Chemical Society: Washington, DC
    • (b) Ellis, S. M.; Balza, F.; Constabel, P.; Hudson, J. B.; Towers, G. H. N. In Light-Activated Pest Control; ACS Symposium Series 616; Heitz, J. R., Downum, K. R., Eds.; American Chemical Society: Washington, DC, 1995; pp 164-178.
    • (1995) Light-Activated Pest Control , pp. 164-178
    • Ellis, S.M.1    Balza, F.2    Constabel, P.3    Hudson, J.B.4    Towers, G.H.N.5
  • 16
    • 84889513967 scopus 로고    scopus 로고
    • 6d
    • 6d
  • 18
    • 84889545431 scopus 로고    scopus 로고
    • 7b
    • 7b
  • 20
    • 84889536674 scopus 로고    scopus 로고
    • 7d
    • 7d
  • 22
    • 84889534411 scopus 로고    scopus 로고
    • note
    • 2c The sample in an NMR tube was deaerated by three freeze-pump-thaw cycles.
  • 23
    • 84889518810 scopus 로고    scopus 로고
    • note
    • (b) Samples in NMR tubes cooled with dry ice/acetone in Dewar flasks were irradiated using a Model LE60 Light Engine (General Electric Company; equipped with a 60 W metal halide lamp and a fiber optic bundle) or with focused light from a Sylvania 300 W lamp, both with output predominantly in the visible spectrum.
  • 24
    • 84889509415 scopus 로고    scopus 로고
    • note
    • Irradiation of unsymmetrical la gives isomeric photoproducts 4a and 4a', in a 97:3 ratio. For clarity only one isomer is shown in Scheme 1. Efforts are underway to determine which isomer predominates and provide an explanation for the surprising regioselectivity of the process.
  • 25
    • 84889535726 scopus 로고    scopus 로고
    • note
    • (a) Identified by comparison with a commercial sample.
  • 27
    • 84889520431 scopus 로고    scopus 로고
    • note
    • (c) We thank Professor Nakayama for an authentic sample of 8 for comparison purposes.
  • 28
    • 84889537789 scopus 로고    scopus 로고
    • max 252.7, 309.6 nm
    • max 252.7, 309.6 nm.
  • 29
    • 84889551958 scopus 로고    scopus 로고
    • note
    • 12c
  • 36
    • 84889502641 scopus 로고    scopus 로고
    • note
    • (a) See the supporting information for details.
  • 37
    • 84889547573 scopus 로고    scopus 로고
    • max ca. 215, 274, 327 (sh) nm. tailing out to ca. 700 nm
    • max ca. 215, 274, 327 (sh) nm. tailing out to ca. 700 nm.
  • 38
    • 84889546757 scopus 로고    scopus 로고
    • 2 together with unknown material. No 2b or 7 was observed in the IR by comparison to authentic material. No discrete products could be identified upon warming a 2-methylpentane matrix containing 9
    • 2 together with unknown material. No 2b or 7 was observed in the IR by comparison to authentic material. No discrete products could be identified upon warming a 2-methylpentane matrix containing 9.
  • 40
    • 0000840877 scopus 로고
    • Barton, D., Ollis, W. D., Eds.: Pergamon: New York
    • (b) Duus, F. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.: Pergamon: New York, 1979; Vol. 3, p 373.
    • (1979) Comprehensive Organic Chemistry , vol.3 , pp. 373
    • Duus, F.1
  • 42
    • 84889517378 scopus 로고    scopus 로고
    • Laser flash photolysis experiments were carried out at Ohio State University in the laboratories of Professor M. S. Platz
    • Laser flash photolysis experiments were carried out at Ohio State University in the laboratories of Professor M. S. Platz.
  • 43
    • 84889553439 scopus 로고    scopus 로고
    • However, cZt-3b → 9 is predicted by ab inmo calculations (HF, 6-31G*) to be themodynamically unfavorable by ca. 10 kcal/mol
    • However, cZt-3b → 9 is predicted by ab inmo calculations (HF, 6-31G*) to be themodynamically unfavorable by ca. 10 kcal/mol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.