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A non-tetradecarboxylative synthesis of 2,7,12,17-tetraphenylporphycene
Journal of Porphyrins and Phthalocyanines ( IF 0.9 ) Pub Date : 2002-08-25 , DOI: 10.1002/jpp.552
ANA GAVALDA 1 , JOSÉ I. BORRELL 1 , JORDI TEIXIDO 1 , SANTIAGO NONELL 1 , OFIR ARAD 1 , ROSER GRAU 1 , MAGDALENA CAÑETE 2 , ANGELES JUARRANZ 2 , ANGELES VILLANUEVA 2 , JUAN C. STOCKERT 2
Affiliation  

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.

中文翻译:

2,7,12,17-四苯基卟啉的非四脱羧合成

报道了一种通过中间体四羧酸 8 升华避免四脱羧基的 2,7,12,17-四苯基卟啉 (2e, TPPo) 的新合成方法。因此,使用带有两个正交酯基团的吡咯 13a 可以合成联吡咯 12a,从中选择性地去除苄酯基团以提供二酯 11。后者通过使用 McFayden-Stevens 反应转化为二醛 10,因此避免在8的四脱羧过程中形成不稳定的联吡咯9。
更新日期:2002-08-25
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