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Tetrahedron Letters
Volumn 18, Issue 43, 1977, Pages 3829-3830
Reduction of organic halides by means of CrCl3-LiAlH4 reagent in anhydrous media
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Indexed keywords

EID: 0000346752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)83365-7     Document Type: Article
Times cited : (103)
References (11)
  • 1
    • 85023293562 scopus 로고
    • Applications of Chromium (II) Salts in Preparative Organic Chemistry
    • (1974) Synthesis , pp. 1
    • Hanson1
  • 8
    • 84918291372 scopus 로고    scopus 로고
    • When the halide was reduced by means of anhydrous chromium(II) chloride purchased from Research Organic/Inorganic Chemical Corp, coupling occurred in a quantitative yield with the ratio of 62%, 27%, and 11%.
  • 9
    • 84918291371 scopus 로고    scopus 로고
    • All attempts to trap the carbenoid failed in the reaction with benzaldehyde or cyclohexene.
  • 10
    • 84918291370 scopus 로고    scopus 로고
    • Typical experimental procedure is as follows. Anhydrous chromium(III) chloride (824 mg, 5.2 mmol) in THF (5 ml) was reduced by portionwise addition of lithium aluminum hydride (98.8 mg, 2.6 mmol) at 0°C. After stirring at room temperature for 10 min the solvent was evaporated in vacuo and the residue was redissolved in DMF (5 ml). Addition of 1, 1-dibromo-2-phenylcyclopropane (289 mg, 1.0 mmol), stirring for 4 hr at room temperature, and the subsequent work-up gave phenylallene (75 mg, 62% yield) upon distillation at 80-95°C/20 Torr (Kugel Rohr) consistent with the authentic spectra. The commercially available anhydrous chromium (II) chloride (see note 7) still involves protic source which hence complicated the reaction path and appreciable amount of phenylcyclopropane was produced.
  • 11
    • 84918291369 scopus 로고    scopus 로고
    • Financial support by the Ministry of Education, Japanese Government, (Grant-in-Aid #247077) is acknowledged.

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