FRIEDEL–CRAFTS REARRANGEMENTS IN BRANCHED CONDENSED RING SYSTEMS: I OCTAMETHYLOCTAHYDROANTHRACENE

Autor:	L. R. C. Barclay, A. H. Gray, C. E. Milligan
Rok vydání:	1961
Předmět:	chemistry.chemical_classification Double bond Organic Chemistry chemistry.chemical_element General Chemistry Conjugated system Ring (chemistry) Chloride Catalysis Hydrocarbon chemistry Aluminium Polymer chemistry medicine Organic chemistry Friedel–Crafts reaction medicine.drug
Zdroj:	Canadian Journal of Chemistry. 39:870-880
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v61-107
Popis:	Treatment of 1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydroanthracene (C22H34, I) with aluminum chloride produced a new hydrocarbon (C22H32, II) containing a conjugated olefinic double bond. Hydrocarbon II was proved to be 1,1,5,5,8,8-hexamethyl-3-isopropyl-5,6,7,8-tetrahydrobenzindene by spectral data, by oxidative studies, and by a synthesis of its reduction product, 1,1,5,5,8,8-hexamethyl-3-isopropyl-5,6,7,8-tetrahydrobenzindane (III). A benzenonium ion mechanism is postulated to explain the 1,2-phenyl shift accompanied by dehydrogenation in the formation of II from I. The detection of hydrogen in the off gas of the rearrangement supports this mechanism. A similar benzenonium ion mechanism can be applied to elucidate the mechanism of isomerization of tertiary to secondary alkylbenzenes reported in the literature.
Databáze:	OpenAIRE
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