Homoconjugation and transannular orbital interactions detected by photoelectron and carbon-13 NMR spectroscopy. Bicyclo [3.3. 1] nona-3, 7-diene-2, 6-dione and …

…, R Gleiter, TA Robbins, P Chayangkoon…

Index: Doerner, Thomas; Gleiter, Rolf; Robbins, Timothy A.; Chayangkoon, Paochai; Lightner, David A. Journal of the American Chemical Society, 1992 , vol. 114, # 9 p. 3235 - 3241

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Citation Number: 24

Abstract

Conclusions The unimolecular rearrangement of simple nascent a-silylsubstituted carbenium ions in the gas phase has been explored. These incipient carbenium ions undergo 1, Zmigration from silicon to carbon to yield a more stable (thermodynamically) silylenium ion with the following relative migratory aptitude: phenyl> hydrogen>> methyl. These results, together with recent theoretica12* 22 and experimer~ tal~* J~~~~~~~ ...