A series of aliphatic and bridgehead aldehydes were decarbonylated in carbon tetrachloride, which served as an inefficient trap for the intermediate acyl radicals.The products were determined quantitatively, and the trapping efficiencies deduced from the product ratios were found to correlate with the stabilities of the alkyl radicals generated from the aliphatic aldehydes. The assumption that the same correlation applies to the bridgehead aldehydes led to the conclusions that the 1-adamantyl and l-bicyclo[2.2.2]octyl radicals are more stable than t-butyl, while l-bicyclo[2.2.1]heptyl is less stable than n-propyl. 182 (1961).

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Carbonium ions with more than one neighboring group available for interaction with the cation center are an unexplored class of considerable potential interest. Among the phenomena expected are fluctuating coordinated structures, intramolecular solvation, and possibly pentacoordination of carbon. This paper describes the synthesis of 26 substituted triphenylcarbinols, and the related carbonium ions, as well as five benzophenone derivatives. The subsequent paper details studies on the interaction between the neighboring groups and carbonium ion (and ketone) centers.