ISSN:
0030-493X
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The first step in the unimolecular reaction of metastable protonated alkylbenzenes is the stretching of the C(benzene) - C(α) bond. Therefore, the intermediacy of a π-complex [C6H6, alkyl+] has often been proposed. In this work, the kinetic energy releases associated with the [tert-alkyl]+ product were measured for a large number of [C6H6-CnH2n+1+] (n 〉 3) ions. At least for β-branched alkylbenzenes, it is shown that the chain isomerization which occurs prior to dissociation involves neither the [C6H6, CnH2n+1+] π-complex nor a [C6H7+, alkene] ion-neutral complex. The data are explained by a concerted process in which the stretching of the C(benzene) - C(α) bond is accompanied by the migration of the tertiary β-hydrogen from C(β) to C(α).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/oms.1210280609
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