TY  - JOUR
AB  - The fast ring-to-ring proton transfer in protonated 1,4-bis(-phenylalkyl)cyclohexanes [(5a)+ H]+, [(5b+ H)]+, and [(6)+ H]+ has been studied by chemical ionization mass spectrometry. The cyclohexane-1,4-diyl unit exerts a distinct stereocontrol upon the rate of proton exchange. Complete proton equilibration is found for protonated cis-dibenzylcyclohexane [(5a)+ H]+, whereas in the trans isomer [(5b)+ H]+ the interannular proton transfer is strongly decelerated. The trans-bis(- phenylethyl) homologue [(6)+ H]+ is found to represent an intermediate case. By comparison with simpler protonated diphenylalkanes the rate of the interannular proton transfer for metastable ions [(5b)+ H]+ and [(6)+ H]+ is estimated to lie within the limits 5 × 105 and 106s–1.
DA  - 1990
DO  - 10.1039/P29900000251
LA  - eng
IS  - 2
M2  - 251
PY  - 1990
SN  - 0300-9580
SP  - 251-256
T2  - Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry
TI  - Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-17743061
Y2  - 2024-11-22T01:19:58
ER  -