Zinc-mediated reductive dimerizations of telluroxanthone and selenoxanthone. Tellurium-selenium selectivity

A. Levy, I. Agranat*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Reductive dimerizations of 9H-selenoxanthen-9-one (3) and 9H-telluroxanthen-9-one (4) (1:1) with zinc in boiling AcOH and HCl for 1 hour gave the bistricyclic ethanes 9,9'-bi(9H-selenoxanthene (10), 9,9'-bi(9H-telluroxanthene) (11) and 9-(9'H-telluroxanthen-9'-yl)-9H-selenoxanthene (12) in the ratios 21 (10):35 (11):44 (12) (in addition to 9H-selenoxanthene (13) and 9H-telluroxanthene (14)) Analogous reactions of 4 and 9H-thioxanthen-9-one (9) (1:1) and 3 and 9 (1:1) gave the corresponding bistricyclic ethanes. The reactions were chalcogen selective with a preference towards the tellurium-bridged bistricyclic ethanes. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)6157-6160
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number32
DOIs
StatePublished - 5 Aug 2000

Keywords

  • Te and Se NMR
  • Bistricyclic ethanes
  • Chalcogen-heterocyclics
  • Overcrowding
  • Reductive couplings

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