1-(2,4,6-tri-tert-butylphenyl)-3-methylphosphole: A phosphole with a significantly flattened phosphorus pyramid having pronounced characteristics of aromaticity

György Keglevich, Zsolt Böcskei, György Miklós Keserü, Kálmán Újszászy, Louis D. Quin

Research output: Contribution to journalArticle

88 Citations (Scopus)

Abstract

Single-crystal X-ray analysis of 1-(2,4,6-tri-tert-butylphenyl)-3- methylphosphole, synthesized to test the effect of the strongly sterically demanding P-substituent on the geometry of the molecule, revealed that the phosphorus pyramid was drastically flattened; the normal out of plane angle of 65°(formed between the P-substituent and the ring C2-P-C5 plane) was reduced to 45.9°. Consistent with strong electron delocalization, the C3- C4 bond length was dramatically shortened relative to that for other phospholes, and the Bird index of aromaticity was 56.5, almost the equivalent of that in pyrrole (59). The phosphole ring, normally resistant to electrophilic substitutions, underwent reaction with acetyl chloride-aluminum chloride, consistent with considerable cyclic electron delocalization.

Original languageEnglish
Pages (from-to)5095-5099
Number of pages5
JournalJournal of the American Chemical Society
Volume119
Issue number22
DOIs
Publication statusPublished - Jun 4 1997

    Fingerprint

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this