TY  - JOUR
AB  - The oxidation of various alkylbenzenes (1-17) with excess dimethyldioxirane (DMDO) in homogeneous acetone solutions has been studied. In general, the benzylic methylene and methine C-H bonds were oxidized to give the corresponding phenones and tertiary benzylic alcohols, respectively, in relatively low yields. Whereas a tert-butyl substituent at the reaction centre leads to very low conversion due to steric hindrance, the presence of additional phenyl groups appears to favour the oxidation in most, but not all cases. Di- and triphenylmethane (4 and 14) were found to be considerably less reactive than cis-decalin. By contrast, the intramolecular competitive oxidation of isobutylbenzene (19) and 1-methyl-4-phenylcyclohexanes (20) reveals that the benzylic C-H bonds are slightly more reactive than the tertiary ones at remote positions.
DA  - 1991
DO  - 10.1515/znb-1991-0915
KW  - Dioxiranes
KW  - Alkylbenzenes
KW  - Dimethyldioxirane
KW  - Oxidation
LA  - eng
IS  - 9
M2  - 1223
PY  - 1991
SN  - 0340-5087
SP  - 1223-1226
T2  - Zeitschrift für Naturforschung B, Journal of Chemical Sciences
TI  - Oxidations of alkylbenzenes with dimethyldioxirane
UR  - https://nbn-resolving.org/urn:nbn:de:0070-bipr-13211
Y2  - 2024-11-22T03:13:59
ER  -