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Mono-(pentafluorophenyl)porphyrins — useful intermediates in the regioselective synthesis of multifunctionalised porphyrins

✍ Scribed by Susanna J. Shaw; Kerry J. Elgie; Christine Edwards; Ross W. Boyle

Book ID
104260602
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
112 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A method is presented for coupling meso-phenylporphyrins bearing a single pentafluorophenyl ring to thiol substituted molecules. Mild reaction conditions are conducive to the employment of a wide range of thiols including biologically active moieties. Both diphenyl-and tetraphenylporphyrins beating a variety of different substituents on the non-fluorinated rings have been used to demonstrate the wide applicability of the method.

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Regioselective synthesis of multifunctio
Regioselective synthesis of multifunctionalised porphyrins-coupling of mono-(pentafluorophenyl)porphyrins to electrophiles
✍ Susanna J Shaw; Christine Edwards; Ross W Boyle 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 113 KB

A method is presented for the coupling of meso-phenylporphyrins, bearing a single pentafluoropbenyl ring, to electrophilic moieties. Selective displacement of the para fluorine atom, using sodium sulphide, results in a transient thiolate species capable of reacting with electrophiles to give a thioe

Use of orthoesters in the synthesis of m
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The use of two orthoesters, trimethyl orthoacetate and trimethyl orthobenzoate, in the synthesis of porphyrins from 5-phenyldipyrromethanes is described. Previously unreported 5,15-diphenyl-10,20-dimethyl porphyrins can be accessed conveniently by this route. A relationship between the steric bulk o