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Synthesis 2006(5): 799-802  
DOI: 10.1055/s-2006-926336
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reduction of an Amido Zinc(II) Phthalocyanine by Diborane

Cristian A. Strasserta, Lelia E. Diceliob, Josefina Awruch*a
a Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
b INQUIMAE, Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina
Fax: +54(11)45083645; e-Mail: jawruch@ffyb.uba.ar;
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Publication History

Received 22 August 2005
Publication Date:
07 February 2006 (online)

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Abstract

1,2-Dicyano-4,5-di[(N,N-dimethylaminocarbonyl)methoxy]benzene (5) was synthesized in 80% yield from the corresponding 1,2-dibromo derivative 4. Octa(peripheral-amide)substituted zinc(II) phthalocyanine 6 was obtained from 5 and zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Phthalocyanine 7 was prepared via reduction of 6 with diborane. Treatment of 7 with methyl iodide afforded cationic dye 8.

Key words

nucleophilic aromatic substitution - reduction - phthalocyanines