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Wasserstoffübertragungen, 21 [1] Pericyclische Wasserstoff‐Übertragung von 1,2‐Dihydroarenen auf ein Cycloheptin
Author(s) -
Gerres Thomas,
Heesing Albert
Publication year - 1992
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.19921250622
Subject(s) - chemistry , pericyclic reaction , aromatization , substituent , reactivity (psychology) , hydrogen , transition state , kinetic isotope effect , hydrogen atom abstraction , computational chemistry , stereochemistry , deuterium , organic chemistry , atomic physics , physics , medicine , alternative medicine , pathology , catalysis
Hydrogen Transfer Reactions, 21. – On the Pericyclic Hydrogen Transfer from 1,2‐Dihydroarenes to a Cycloheptyne The aromatization of 1,2‐dihydroarenes by thiacycloheptyne 1 takes place by a pericyclic process. This mechanism is supported by the dependence of the reactivity on the π system, absence of both substituent and solvent effects, a strong negative entropy of activation, high stereoselectivity of hydrogen abstraction, as well as size and consistency of primary isotope effects and semiempirical calculations of the transition state.