Premium
Tin for Organic Synthesis, 5 A New and Regioselective Synthesis of Aromatic Diazene Derivatives
Author(s) -
Neumann Wilhelm P.,
Wicenec Christian
Publication year - 1991
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.19911241023
Subject(s) - chemistry , regioselectivity , nitro , azo coupling , electrophilic substitution , diazonium compounds , electrophilic aromatic substitution , tin , electrophile , reaction conditions , organic chemistry , nitro compound , group (periodic table) , combinatorial chemistry , medicinal chemistry , catalysis , alkyl
A new method for the preparation of aromatic diazene derivatives 3a — 1, 5, 7a, b, 9 under very mild conditions is described. The reaction of trialkylarylstannanes with nitro‐substituted benzenediazonium tetrafluoroborates leads, by strict ipso substitution, to the corresponding diaryldiazenes in satisfactory to high yields. Due to the excellent leaving group quality of the stannyl group azo compounds may be prepared which are not accessible by normal electrophilic azo coupling. The products can be valuable precursors, obtained by reduction to the amines or other derivatizations, for consecutive aromatic compounds.