Imidazole-assisted intramolecular phenoxythiocarbonylation of tertiary alcohols. A key reaction for the deoxygenation of α-trifluoromethylarylmethyl alcohols

Fu Lian Hsu, Xiaoyan Zhang, Seoung Soo Hong, Frederic J. Bergt, Duane Miller

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The deoxygenation of α-trifluoromethylarylmethyl alcohols failed under catalytic hydrogenation conditions. However, these alcohols can be deoxygenated via their thionocarbonate intermediates followed by homolytic reductive cleavage of the CO bond. The formation of the phenyl thionocarbonate esters is sterically dependent. Consequently, secondary α-trifluoromethyl arylmethyl alcohols can be smoothly converted to thionocarbonates, but tertiary alcohols cannot. Exceptions to this lack of reactivity are the aryl 4-substituted imidazolyl trifluoromethyl carbinols, which do form the thionocarbonates under these conditions.

Original languageEnglish (US)
Pages (from-to)801-809
Number of pages9
JournalHeterocycles
Volume39
Issue number2
DOIs
StatePublished - Dec 31 1994

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Alcohols
Hydrogenation
Carbon Monoxide
Methanol
Esters
imidazole

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Imidazole-assisted intramolecular phenoxythiocarbonylation of tertiary alcohols. A key reaction for the deoxygenation of α-trifluoromethylarylmethyl alcohols. / Hsu, Fu Lian; Zhang, Xiaoyan; Hong, Seoung Soo; Bergt, Frederic J.; Miller, Duane.

In: Heterocycles, Vol. 39, No. 2, 31.12.1994, p. 801-809.

Research output: Contribution to journalArticle

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