2, 3, 17, 18‐Tetrahalohexaphyrins and the First Phlorin‐type Hexaphyrins. Issue 9 (18th June 2013)

• Record Type: Journal Article
• Authors: Higashino, Tomohiro; Osuka, Atsuhiro
• Is Part Of: Chemistry, an Asian journal. Volume 8:Issue 9(2013:Sep.)
• Page Start: 1994
• Page End: 2002
• Publication Date: 2013-06-18
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201300474
• Languages: English
• ISSNs: 1861-4728

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>1‐(Triisopropylsilyl)‐3, 4‐dichloropyrrole and 1‐(triisopropylsilyl)‐3, 4‐difluoropyrrole were conveniently prepared from the corresponding 3, 4‐dibromopyrrole by <named-content id="d407e798" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">lithiation</named-content> followed by <named-content id="d407e801" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">halogenation</named-content>. 2, 3, 17, 18‐Tetrahalogeno [26]‐ and [28]hexaphyrins have been prepared by condensation of 3, 4‐dihalopyrroles and a dipyrromethane‐dicarbinol. 2, 3, 17, 18‐Tetrahalogenated hexaphyrins display variable structural and electronic properties depending upon the halogen atom and the number of π‐electrons. Tetrabromo[28]hexaphyrin and tetrachloro[28]hexaphyrin were further reduced with excess NaBH₄ to furnish <italic>meso</italic>‐reduced hexaphyrins as the first example of phlorin‐type <italic>meso</italic>‐aryl‐substituted hexaphyrins.</p> </abstract>