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Volumn , Issue 2, 2006, Pages 351-370

Photoreactions of tricyclic α-cyclopropyl ketones and unsaturated enones - Synthesis of polyquinanes and analogous ring systems

Author keywords

Photoinduced electron transfer; Polycycles radical ions; Polyquinanes; Tandem fragmentation cyclization

Indexed keywords


EID: 31144464254     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500546     Document Type: Article
Times cited : (26)

References (65)
  • 1
    • 0037548585 scopus 로고    scopus 로고
    • B. G. Teubner, Stuttgart-Leipzig
    • E. Breitmaier, Terpene, B. G. Teubner, Stuttgart-Leipzig, 1999.
    • (1999) Terpene
    • Breitmaier, E.1
  • 2
    • 0004215279 scopus 로고
    • S. Hirzel Press, Stuttgart
    • nd ed., S. Hirzel Press, Stuttgart, 1990.
    • (1990) nd Ed.
    • Nuhn, P.1
  • 40
  • 49
    • 31144459409 scopus 로고    scopus 로고
    • PhD Thesis, University of Bielefeld, Germany
    • The X-ray analysis was performed from the crystalline state of the ketal product: (7a′ S*)-7a′-prop-2″-ynyl-1′,2′, 4′,6′,7′,7a′-hexahydrospiro[1,3-dioxolan-2, 5′-indene] (see also N. T. Tzvetkov, PhD Thesis, University of Bielefeld, Germany, 2005).
    • (2005)
    • Tzvetkov, N.T.1
  • 52
    • 31144434494 scopus 로고    scopus 로고
    • note
    • Corey cyclopropanation of the compound 5 resulted predominantly in the formation of a 93:7 diastereomeric mixture of trans-and cis-oxirane products.
  • 54
    • 31144479516 scopus 로고    scopus 로고
    • CCDC-276396 (rac-18) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 56
    • 31144478994 scopus 로고    scopus 로고
    • PhD Thesis, University of Bielefeld (Germany)
    • N. T. Tzvetkov, PhD Thesis, University of Bielefeld (Germany), 2005.
    • (2005)
    • Tzvetkov, N.T.1
  • 58
    • 31144473744 scopus 로고    scopus 로고
    • note
    • 2 in THF in the presence of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)- pyrimidinone (DMPU) as an additive. The product 30 (35%) was isolated by column chromatography (cyclohexane/EtOAc, 90:10) as a colourless oil.
  • 59
    • 31144464324 scopus 로고    scopus 로고
    • note
    • All calculations were carried out with Titan V1.05, Schrödinger Inc., Wavefunction Inc., 2000.
  • 61
    • 31144457329 scopus 로고    scopus 로고
    • note
    • For the calculations of the energy profiles of the corresponding 6-endo and 5-exo radicals we used a combination of the B3LYP level and the 6-31G* basis set. The conformational analysis and the transition states were calculated at a semiempirical level (AM1).
  • 65
    • 31144461187 scopus 로고    scopus 로고
    • note
    • 2 afforded a mixture of the compounds 31 and 34 in 18% combined yield as well as the non-cyclized product 33 in 3% yield after chromatographic purification (cyclohexane/EtOAc 80:20). The product ratio was determined by GC as 2:1 (34:31).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.