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A non-tetradecarboxylative synthesis of 2,7,12,17-tetraphenylporphycene

Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain

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JOSÉ I. BORRELL

Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain

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JORDI TEIXIDO

Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain

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SANTIAGO NONELL

Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain

Corresponding author, Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain.

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OFIR ARAD

Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain

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ROSER GRAU

Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain

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MAGDALENA CAÑETE

Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain

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ANGELES JUARRANZ

Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain

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ANGELES VILLANUEVA

Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain

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, and

JUAN C. STOCKERT

Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain

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https://doi.org/10.1002/jpp.552Cited by:20 (Source: Crossref)

Abstract

A new synthetic method for 2,7,12,17-tetraphenylporphycene (2e, TPPo) which avoids tetradecarboxylation by sublimation of the intermediate tetracarboxylic acid 8 is reported. Thus, the use of a pyrrol 13a bearing two orthogonal ester groups allows the synthesis of bipyrrol 12a, from which the benzyl ester groups are selectively removed to afford diester 11. The latter is transformed to dialdehyde 10 by using the McFayden–Stevens reaction, thus avoiding the unstable bipyrrol 9 formed during the tetradecarboxylation of 8.

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