Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit

Kuck D, Thölmann D, Grützmacher H-F (1990)
Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry 1990(2): 251-256.

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Abstract
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.
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Kuck D, Thölmann D, Grützmacher H-F. Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry. 1990;1990(2):251-256.
Kuck, D., Thölmann, D., & Grützmacher, H. - F. (1990). Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry, 1990(2), 251-256.
Kuck, D., Thölmann, D., and Grützmacher, H. - F. (1990). Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry 1990, 251-256.
Kuck, D., Thölmann, D., & Grützmacher, H.-F., 1990. Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry, 1990(2), p 251-256.
D. Kuck, D. Thölmann, and H.-F. Grützmacher, “Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit”, Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry, vol. 1990, 1990, pp. 251-256.
Kuck, D., Thölmann, D., Grützmacher, H.-F.: Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry. 1990, 251-256 (1990).
Kuck, Dietmar, Thölmann, Detlef, and Grützmacher, Hans-Friedrich. “Fast interannular proton transfer in gaseous protonated [alpha, omega]-diphenylalkanes: stereocontrol by the cyclohexane-1,4-diyl unit”. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry 1990.2 (1990): 251-256.
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