ISSN:
0009-2940
Keywords:
Free-radical additions
;
Alkyl radicals
;
Stereoselectivity
;
Hydrogen transfer
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The addition of cyclohexane to alkylmaleic anhydrides 1a-f via cyclic radicals 2a-f gave a mixture of (Z)- and (E)-2,3-dialkylsuccinic anhydrides 3a-f. The stereoselectivity of the hydrogen transfer from cyclohexane to radicals 2a-d was measured in the temperature range of 200-260°C, and the relative activation parameters of the formation of (Z)- and (E)-3 were determined. The stereoselectivity of the hydrogen transfer from cyclohexylmercuric hydride at 25°C was measured as well. The results are rationalized assuming steric interactions in the transition state of H donor and β substituent and of α and β substituent, respectively. An X-ray structure analysis of the highly strained addition product (Z)-3d was performed.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270616
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