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Wasserstoffübertragungen, 16. Freie 1‐Phenylallyl‐Kationen bei der Aromatisierung von Dihydronaphthalinen mit Triphenylmethyl‐tetrafluoroborat
Author(s) -
Giese Georg,
Heesing Albert
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901231220
Subject(s) - chemistry , tetrafluoroborate , hydride , medicinal chemistry , kinetic isotope effect , deuterium , hydrogen , organic chemistry , catalysis , ionic liquid , physics , quantum mechanics
Free 1‐Phenylallyl Cations in the Aromatisation of Dihydronaphthalenes by Triphenylmethyl Tetrafluoroborate The aromatisation of 1,2‐ and 1,4‐dihydronaphthalenes by trityl cations proceeds by a common intermediate, the 1‐phenylallyl cation 4 of sufficient lifetime to allow for both side reactions and loss of stereoselectivity. The primary hydride abstraction occurs with moderate tunneling participation and in a linear geometry of the three participating atoms as shown by the temperature dependence of the primary isotope effect.