1-Manxyl: A persistent tertiary alkyl radical that disproportionates via ε-hydrogen abstraction

Journal of the American Chemical Society

Volumn 118, Issue 48, 1996, Pages 12232-12233

  Crǎciun, Liliana ^a   Jackson, James E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; MOLECULAR DYNAMICS; THERMODYNAMICS;

EID: 0030443644     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961136t     Document Type: Article

References (39)

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38. This process is reminiscent of the case of halobicyclo[1.1.1]pent-1-yl radicals, where evidence was found for a new γ-disproportionation process in which the γ-fluorine (or chlorine) atom was transferred from the 3-fluoro (or 3-chloro) radical to a triethylsilyl or to a second bicyclo[1.1.1]pent-1-yl radical to yield, in both cases, [1.1.1]propellane. Adcock, W.; Binmore, G. T.; Krstic, A. R.; Walton, J. C.; Wilkie, J. J. Am. Chem. Soc. 1995, 117, 2758.
39. Our thanks go to Professor Roger Alder, who kindly provided us with [3.3.3]propellanedione, converted to [3.3.3]propellane by Kishner-Wolff reduction according to the literature procedure. Weber, R. W.; Cook, J. M. Can. J. Chem. 1978, 56, 189.