Selective synthesis of meso-naphthylporphyrins
Selective synthesis of meso-naphthylporphyrins
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DOI：
10.1021/jo0260488
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发表时间：
2002-10-18
影响因子：
3.6
通讯作者：
Öztürk, O
中科院分区：
文献类型：
--
作者：
Cammidge, AN;Öztürk, O
合成了一系列新型的中位(8-取代-1-萘基)卟啉类化合物，使其在卟啉平面上具有紧密的识别环境。讨论了单一阿托品的选择性合成。双萘甲醛12与苯基二吡咯甲烷的缩合反应意外地导致了α，α-5，10-桥联异构体14的选择性合成。对这种不寻常的杂乱现象提出了一种机理，并描述了α，α-5，15-双萘基卟啉的替代合成。5，15-类似物的合成可以通过使用(五氟苯基)二吡咯甲烷或通过预合成二(二吡咯甲烷)衍生物22(由双萘醛12合成)，然后与苯甲醛缩合来实现。
A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the alpha,alpha-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of alpha,alpha-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.