Synthesis and characterisation of labelled diphenylcarboranes

Susan Robertson, David Ellis, Thomas D. McGrath, Georgina M. Rosair, Alan J. Welch

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18 Citations (Scopus)


The synthesis, by either acid-catalysed electrophilic substitution or recapitation, and characterisation of four new B-labelled diphenyl carboranes is described. Two of these, 1,2-Ph2-9,12-I2-1,2-closo-C2 B10H8 (1) and 1,2-Ph2-3-Me-1,2-closo-C2B10H9 (2) were subjected to crystallographic study, whilst the 3-Et (3) and 3-F (4) analogues of 2 were studied spectroscopically. Decapitation of the mono-iodo analogue of I affords [5-I-7,8-Ph2-7,8-nido-C2B9 H9]-, isolated as [HNEt3]+ (5a) [HNMe3]+ (5b) and [C6H5CH2NMe3]+ (5c) salts, the last of which was subjected to crystallographic analysis. Decapitation of 3 and 4 selectively removes B6, yielding the 3-labelled nido-carboranes [3-Et-7,8-Ph2-7,8-nido-C2B9 H9]- and [3-F-7,8-Ph2-7,8-nido-C2B9 H9]-, respectively, both isolated as [HNMe3]+ salts (6a and 7). The ethyl species was also prepared as the [HNEt3]+ salt (6b), and was structurally characterised. Salts 5b, 6a and 7 are all afforded in good yield and the anions are ideal candidates for subsequent deprotonation and metallation, which should result in low-temperature isomerisation of the transient 3,1,2-MC2B9 species thereby produced, and thereby yield important, robust, mechanistic information on the rearrangement process. © 2003 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1293-1301
Number of pages9
Issue number10
Publication statusPublished - 15 May 2003


  • Carborane
  • Crystallographic study
  • Isomerisation
  • Spectroscopy
  • Synthesis
  • Vertex labelling


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