Dissimilar reactivities of diastereomeric 1,1,1-trifluoro-3-(4-methoxyphenyl)-2,3-diphenylpropan-2-ols in an attempted elimination reaction

Gyula Hornyák, Jozsef Fetter, Karoly Lempert, Laszlo Párkányi, Gabor Németh, Laszlo Poszávácz, Gyula Simig

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Attempted dehydration of a diastereomeric mixture of 1,1,1-trifluoro-3-(4-methoxyphenyl)-2,3-diphenyl-propan-2-ols (6a) with thionyl chloride in the presence of pyridine afforded the rearranged derivative 8 as the main product and only small amounts of the expected olefins (4, 5). Similar treatment of (2RS,3RS)-6a gave the rearrangement product 8 exclusively, while transformation of (2RS,3SR)-6a resulted in the formation of compounds 4, 5 and 8. The different reactivity of the diastereomers is rationalised.

Original languageEnglish
Pages (from-to)239-244
Number of pages6
JournalJournal of Fluorine Chemistry
Volume108
Issue number2
DOIs
Publication statusPublished - Jan 1 2001

Keywords

  • Destabilised carbocation
  • Diastereospecific reaction
  • Field effect
  • Trifluoromethyl group substituent effect
  • Wagner-Meerwein type rearrangement of 1-(trifluoromethyl)-1,2,2-triarylethanols

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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