Journal of the American Chemical Society p. 4768 - 4772 (1980)
Update date:2022-08-23
Topics:
Attina, Marina
Cacace, Fulvio
Giacomello, Pierluigi
Gas-phase alkylaton of benzene and toluene has been used as a probe to sample the isomeric population of C3H7+ ions obtained from the protonation of cyclopropane and of propene, respectively, with H3+ ions in H2 gas at pressures from 50 to 720 torr.The reagent from cyclopropane promotes extensive (over 40percent) n-propylation, in addition to isopropylation of the arenes, on contrast to the reagent from propene that yields only traces of n-propylated products.The n-propylating reagent is identified as protonated cyclopropane, whose lifetime must exceed 10-7 s in the gaseous systems investigated.The mechanism and the selectivity of the gas-phase alkylation are discussed and compared to relevant mass spectrometric and kinetic results.
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