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1,3‐dioxenium cations: Synthesis, structure and topomerization
Author(s) -
Olekhnovich Evgenii P.,
Arseniev Viacheslav G.,
Kompan Olga E.,
Borodkin Gennadii S.,
Struchkov Yurii T.,
Olekhnovich Lev P.,
Minkin Vladimir I.
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199603)9:3<129::aid-poc762>3.0.co;2-7
Subject(s) - chemistry , perchlorate , perchloric acid , acetic acid , crystal structure , dissociation (chemistry) , crystallography , triad (sociology) , ring (chemistry) , ion , stereochemistry , medicinal chemistry , inorganic chemistry , organic chemistry , psychology , psychoanalysis
Previously unknown 1,3‐dioxenium perchlorates were obtained by coupling 1,3‐diketones with aliphatic ketones in an acetic acid solution of perchloric acid. The dioxenium ring of 4,6‐bis( p ‐methoxystyryl)‐2,2‐pentamethylenespiro‐1,3‐dioxenium perchlorate in the crystal possesses the envelope conformation, the geometry of the carbon triad being close to that of the allyl cations. Variable‐temperature 1 H NMR spectra of unsymmetrical 1,3‐dioxenium cations revealed the occurrence of a sufficiently fast enantiotopomerization process governed by the C(SINGLE BOND)O bond dissociation‐recombination mechanism.