Symmetrical spiro-phosphoroheterocycles from the selenation of carbohydrazides

Guoxiong Hua, David B. Cordes, Yang Li, Alexandra M. Z. Slawin, J. Derek Woollins

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) reacts with benzoic hydrazides in refluxing toluene to give new symmetrical spiro heterocycles in 48-76% isolated yields. However, under identical conditions, treating Woollins' reagent with thiophene-2-carbohydrazide leads to an additional product, 1,3,4-selenadiazole (27% yield) together with the spiro phosphorus heterocycle in 44% yield. Three representative X-ray structures are reported. (C) 2011 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3311-3314
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number26
DOIs
Publication statusPublished - 29 Jun 2011

Keywords

  • Phosphorus
  • Selenium
  • Heterocycle
  • Woollins' reagent
  • X-ray structure
  • Spiro compounds
  • MOLECULAR STRUCTURE
  • CRYSTAL-STRUCTURES
  • HETEROCYCLES
  • REACTIVITY

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