T. Kinoshita, T. Yokoi, K. Takeuchi
1992
Citations
0
Influential Citations
2
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
2,2-Dimethyl-1-(p-methoxyphenyl)propyl cation has been generated by treatment of the corresponding chloride with AgSbF6 in SO2–CH2Cl2(20% CD2Cl2) at –98 °C and its 13C NMR spectrum observed. The reactions of the generated carbocation with methanol or phenol give products with a rearranged carbon atom skeleton and non-rearranged products with complete racemization, as expected for a typical carbocation reaction, whereas the solvolysis of the corresponding p-nitrobenzoate in phenol affords exclusively the non-rearranged products with partial retention of configuration. Such distinctions between generated carbocation reactions and the solvolysis reactions indicate that no dissociated (free) carbocation intermediate intervenes even in this solvolysis system, i.e., it is one of a few systems which have been hitherto confirmed to proceed via multiple intermediate stages.