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1‐Phenalenol: Isolation and Disproportionation
Author(s) -
Sugihara Yoshikazu,
Kawanaka Hidetoshi,
Murata Ichiro
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198912681
Subject(s) - disproportionation , reagent , chemistry , dilution , isolation (microbiology) , ion , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , thermodynamics , physics , biology , microbiology and biotechnology
A large excess of reducing agent and high‐dilution techniques permitted isolation of 1 in accordance with reaction (a). Disproportionation of 1 to phenalene and phenalenone is greatly accelerated by protic reagents : no reaction in CDCl 3 , but a half‐life of only 30 min upon addition of HOAc (HOAC: 1 = 1:30). Carbinols derived from stable carbenium ions are normally quite labile, so the procedure illustrated here is of general significance.