Small-Ring Compounds. XXXIV. Carbonium Ion Reactions of 1-Methylcyclobutyl, (1-Methylcyclopropyl)-carbinyl and (β-Methylallyl)-carbinyl Derivatives1

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Abstract

(1-Methylcyclopropyl)-carbinyl chloride was found to solvolyze in 50% aqueous ethanol ca. ten times faster than 1-methylcyclobutyl chloride and as fast as t-butyl chloride. Treatment of (1-methylcyclopropyl)-carbinylamine and 1-methylcyclobutylamine with nitrous acid gave only 1-methylcyclobutanol. (β-Methylallyl)-carbinylamine gave the same alcohol as the only cyclic product. About 3% of the ^(14)C content of 1-methylcyclobutanol from the deamination of (1-methylcyclopropyl)-carbynil-α-^(14)C)-amine was found at the 3-position. These results are interpretable in terms of classical carbonium ions and/or substituted “bicyclobutonium” ion intermediates with fairly localized positive charges.

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