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The effect of substrate structure on the direction of cyclization of ortho-alkynylbenzene diazonium salts

โœ Scribed by Lidiya G. Fedenok; Mark S. Shvartsberg; Valentina S. Bashurova; George A. Bogdanchikov

Book ID
104097093
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
258 KB
Volume
51
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The cyclization of ortho-(arylethynyl)benzene diazonium salts (the Richter reaction) is studied. A reaction mechanism, which differs radically from that reported earlier is proposed and substantiated by experimental data and quantum-chemical calculations.

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Cyclization of ortho-(phenylethynyl)benzene diazonium salts containing groups of +C character at the para-position of the phenyl ring proceeds with closure to a pyrazole, but not to a pyridazine as is the case in the presence of neutral or -C groups.