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Cyanuric chloride–dimethylformamide mediated cleavage of cyclopropylcarbinols-synthesis of phenolic antioxidant and construction of a new vinylcyclopropane skeleton

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Identifiers
DOI: 10.1016/j.tetlet.2014.07.053
Keywords
  • Cyclopropylcarbinol
  • Cyanuric Chloride
  • Cleavage
  • Homoallylic Chloride
  • Diene

Abstract

Abstract Differently substituted cyclopropylcarbinols underwent ring cleavage with easily accessible cyanuric chloride–N,N-dimethylformamide adduct to produce homoallylic chlorides or dienes depending on the nature and location of the substituents. A mechanistic explanation of the aforesaid observations has been provided. A promising antioxidant compound was prepared following this protocol and studied against Fenton’s reagent. This methodology was utilized to construct hitherto unreported vinylcyclopropane frameworks bearing homoallylic chloride and diene moieties.

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