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Alkali metal mediated conversion of arene oxides and arene imines into aromatic hydrocarbons
Author(s) -
Elmalak Omar,
Rabinovitz Mordecai,
Blum Jochanan
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300151
Subject(s) - chemistry , deoxygenation , chrysene , anthracene , phenanthrene , tetrahydrofuran , alkali metal , lithium (medication) , metal , deamination , photochemistry , organic chemistry , inorganic chemistry , medicinal chemistry , catalysis , medicine , solvent , endocrinology , enzyme
Abstract K‐Region oxides and imines of phenanthrene, chrysene benz[ a ]anthracene, and dibenz[ a,h ]anthracene react in tetrahydrofuran with lithium and sodium to give the parent hydrocarbons. In the presence of excessive metal, the latter are converted into dianions from which the parent compounds can be regenerated upon quenching with oxygen. Metalate derivatives of the oxides and imines are proposed to be the corresponding reaction intermediates in the deoxygenation and deamination processes.