The gas-phase attacks of Broensted acids, CnH5+ (n = 1, 2), obtained by radiolysis of CH4 by 60Co, on RCHR1CHROH (R = H, Me, R1 = Cl, Br; R = H, R1 = F), were studied. The nature and the isomeric distribution of the neutral products show that extensive gas-phase neighboring group participation, involving the intermediacy of an O-protonated alkene oxide, occurs in these reactions.
Direct evidence of neighboring group participation in the gas phase / Angelini, Giancarlo; Speranza, Maurizio. - In: JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS. - ISSN 0022-4936. - STAMPA. - 5(1978), pp. 213-214.