Oxidative functionalization of adamantane and some of its derivatives in solution

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1413-1420

  Mella, M ^a   Freccero, M ^a   Soldi, T ^a   Fasani, E ^a   Albini, A ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001085303     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951645y     Document Type: Article

References (65)

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55. (a) Notice also that in the TCB reaction a small amount of the 6-alkylated benzenetetracarbonitrile (5), resulting from the alkylation at one of the unsubstituted positions, is formed besides the usual product of ipso substitution, viz. the 5-alkylated benzenetricarbonitrile (4), which, at any rate, remains the main one. A case of attack at the unsubstituted position of TCB has been previously observed, again as a minor path and again with an ether, 1,4-dioxane, ref 15b. We suggested that this products arises from an alternative mechanism, e.g., direct proton transfer within the contact radical ion pair (or exciplex) which has probably a different conformation when the donor contains an oxygen atom than when it is a hydrocarbon, ref 15b. At any rate this remains a minor path and has no bearing on the main mode of fragmentation of the radical cation.
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