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Cyclometalation of arylazo compounds. Part 2Regioselectivity of the Cyclopalladation of Some Substituted 1-Arylazonaphthalenes. 2nd Communication on Compounds with a Metal-Arene σ-Bond

✍ Scribed by Max Hugentobler; Alfred J. Klaus; Hanspeter Mettler; Paul Rys; Gabi Wehrle

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
662 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A variety of cyclopalladated 1‐arylazonaphthalenes is described, where ortho‐palladation occurs at C(2) in the naphthyl ring or at C(2′ or 6′) in the phenyl moiety. Two examples of Peri‐cyclopalladation at C(8) in the naphthyl ring are presented. The electronic and steric‐influences of substituents at either arene moiety on the relative basicities of the azo‐N‐atoms and the relative nucleophilicities of the potential palladation sites C(2), C(2′ or 6′), and C(8) are discussed qualitatively in order to rationalize the observed regioselectivity.

📜 SIMILAR VOLUMES

Cyclometalation of Arylazo Compounds. Pa
Cyclometalation of Arylazo Compounds. Part 1 synthesis and cyclopalladation of some substituted 1-arylazonaphthalenes. 1st Communication on compounds with a metal-arene σ-bond
✍ Alfred J. Klaus; Paul Rys 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 958 KB

## Abstract The syntheses of 1‐phenylazonaphthalene (**1a**) and its [3′‐methyl‐ (**1b**), 4′‐methoxy‐ (**1c**), 3′‐methoxy‐ (**1d**)] derivatives are described. Cyclopalladation of these azo ligands with Pd(II) acetate or Na~2~PdCl~4~ leads to complexes with Pd(II) coordinated on the azo N~β~‐atom

Cyclometalated Arylazo Compounds. Part 4
Cyclometalated Arylazo Compounds. Part 4. ortho-cyano-1-arylazonaphthalenes and 3-amino-2-arylbenzo [g]indazoles from cyclopalladated 1-arylazonaphthalenes. 4th communication on compounds with a metal-arene σ-bond
✍ Kurt Gehrig; Alfred J. Klaus; Paul Rys 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 297 KB

## Abstract The reaction of a cyclopalladated 1‐arylazonaphthalene with tetrabutylammonium cyanide leads to an __ortho__‐cyano‐1‐arylazonaphthalene and a 3‐amino‐aryl‐benzo[g]indazole, depending upon whether triphenylphosphine or 1,2‐bis(diphenyl‐phosphino)ethane (DIPHOS) is used to monomerize the