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• W2950067660 startingPage "3362" @default.
• W2950067660 abstract "A series of 2,5(or 1,4)-dihaloadamantanes (4 and 5, X = Y = halogens) and 9,10-dihalotriptycenes (7, X = Y = halogens) as well as two 5-halo (X) adamantan-2-ones (6, Y = O, X = Br and I) have been treated with Me(3)SnLi in THF in the absence and presence of tert-butylamine (TBA) and dicyclohexylphosphine (DCHP). The product distributions of these reactions have been established by (13)C and (119)Sn NMR spectroscopy, vapor-phase chromatographic analyses, and GC/MS. The former compounds (4 and 5) appear to react exclusively by a free-radical chain process (S(RN)1 mechanism) to yield tin substitution products. By contrast, the triptycenes react predominantly by a polar mechanism initiated by the formation of a carbanion. In the case of the halo ketones (6, Y = O, X = Br and I), a mechanistic divergence of the reaction was unexpectedly encountered. Whereas the bromo ketone provides the substitution product (6, Y = O, X = SnMe(3)) in good yield (ca. 75%), apparently by a radical pathway, the iodo ketone yields a fragmentation product (ca. 95% yield) by a polar mechanism. This mechanistic switch highlights the importance of the electronegativity of the leaving group as well as substituent-induced electron delocalization as molecular factors governing the competition between radical and polar pathways." @default.
• W2950067660 created "2019-06-27" @default.
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• W2950067660 date "2001-04-25" @default.
• W2950067660 modified "2023-09-23" @default.
• W2950067660 title "Nucleophilic Substitution Induced by Electron Transfer at the Bridgehead of Polycyclic Alkanes: Competition between Polar and Radical Pathways" @default.
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• W2950067660 doi "https://doi.org/10.1021/jo001638w" @default.
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