Divergent pathways in the rearrangement of tricyclo[3.3.0.02,4]octanes (housanes) on chemical electron transfer (CET) versus acid catalysis: A comparison of radical cations and carbocations

Journal of the American Chemical Society

Volumn 120, Issue 4, 1998, Pages 831-832

  Adam, Waldemar ^a   Handmann, Vera Iris ^a   Kita, Fumio ^a   Heidenfelder, Thomas ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; METHYL GROUP; OCTANE; RADICAL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; ELECTRON TRANSPORT; NONHUMAN; OXIDATION;

EID: 0032481405     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9732340     Document Type: Article

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14. 2d The preference for the exo diastereomer is due to the larger steric interaction of the endo-methyl group at the 2 position with the annellated cyclopentane ring, analogous to the explanation offered for the exo diastereoselectivity observed for the carbocation. (b) Presumably, the different reaction times required in the CET mode derive from the different oxidation potentials of the housanes 1.
15. ox data is available for the remaining radicals.
16. ox data is available for the remaining radicals.
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