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Volumn 8, Issue 5, 2006, Pages 388-390

Engineering acyclic alkyl aryl ketones for enantioselective Norrish/Yang type II photochemistry in the crystalline state

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EID: 33745010928     PISSN: 14668033     EISSN: 14668033     Source Type: Journal    
DOI: 10.1039/b601903j     Document Type: Article
Times cited : (15)

References (16)
  • 8
    • 33745011026 scopus 로고    scopus 로고
    • Typical primary/secondary/tertiary rate ratios for γ-hydrogen atom abstraction of γ-substituted butyrophenones are approximately 1 : 30 : 200 per hydrogen2
    • 2) was 0.124 (all data)
  • 9
    • 33745040133 scopus 로고    scopus 로고
    • Prolonged irradiation of compound 3b in acetonitrile gave rise to a myriad of type I and type II products that we did not bother to characterize fully
    • Prolonged irradiation of compound 3b in acetonitrile gave rise to a myriad of type I and type II products that we did not bother to characterize fully
  • 10
    • 33745021509 scopus 로고    scopus 로고
    • Molecular mechanics calculations were carried out using HyperChem/ChemPlus version 5.11/2.0
    • Molecular mechanics calculations were carried out using HyperChem/ChemPlus version 5.11/2.0
  • 11
    • 33745029970 scopus 로고    scopus 로고
    • For comparable studies on 2-methyl-1-phenylbutan-1-one, see
    • Ratio based on GC uncorrected for detector response at low conversion (5%)
  • 12
    • 0001732887 scopus 로고
    • 2) was 0.357 (all data). CCDC reference numbers 297457 and 297458. For crystallographic data in CIF or other electronic format see DOI: For a description of the solid state photolysis and workup technique, see
    • F. D. Lewis T. A. Hilliard J. Am. Chem. Soc. 1972 94 3852
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 3852
    • Lewis, F.D.1    Hilliard, T.A.2
  • 14
    • 33745045336 scopus 로고    scopus 로고
    • In this case and the others summarized in Table 1, a small amount of cleavage was detectable by GC when the solid state photolyses were carried out at room temperature
    • In this case and the others summarized in Table 1, a small amount of cleavage was detectable by GC when the solid state photolyses were carried out at room temperature
  • 15
    • 33745039359 scopus 로고    scopus 로고
    • The absolute configurations were not determined experimentally but are based on the known absolute conformation of the starting salt and the assumed mechanism, which is abstraction of Ha followed by least motion biradical cyclization with retention of configuration at the carbonyl carbon. This leads to the experimentally observed Z cyclobutanol (OH and ethyl groups cis)
    • The absolute configurations were not determined experimentally but are based on the known absolute conformation of the starting salt and the assumed mechanism, which is abstraction of Ha followed by least motion biradical cyclization with retention of configuration at the carbonyl carbon. This leads to the experimentally observed Z cyclobutanol (OH and ethyl groups cis)


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