A simple two steps ytterbium triflate‐catalysed preparation of 2,2‐dimethyl‐2 h ‐chromenes from salicylaldehydes and 2‐methylpropene | Zendy

Prado Soizic | Zendy; Janin Yves L. | Zendy; Bost PierreEtienne | Zendy

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A simple two steps ytterbium triflate‐catalysed preparation of 2,2‐dimethyl‐2 h ‐chromenes from salicylaldehydes and 2‐methylpropene

Author(s) -

Prado Soizic,

Janin Yves L.,

Bost PierreEtienne

Publication year - 2006

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570430626

Subject(s) - chemistry , trifluoromethanesulfonate , salicylaldehyde , ytterbium , catalysis , medicinal chemistry , phenol , organic chemistry , stereochemistry , schiff base , physics , optoelectronics , doping

The preparation of various 2,2‐dimethyl‐2 H ‐chromenes was achieved in two steps via an ytterbium triflate‐catalysed reaction between salicylaldehydes, trimethylorthoformate and 2‐methylpropene. From salicylaldehyde, two reaction products were characterised: 4‐methoxy‐2,2‐dimethylchroman and 2‐(1,3‐dimethoxy‐3‐methylbutyl)phenol. The former compound probably results from a Lewis acid‐catalysed [2+4] cycloaddition between the intermediate quinonemethide and 2‐methylpropene whereas the latter may occur via a reaction related to a carbonyl‐ene reaction between the quinonemethide and 2‐methylpropene. Both compounds were subjected to a catalytic acidic treatment leading to 2,2‐dimethyl‐2 H ‐chromene. Starting from various salicylaldehydes, the scope of this method was investigated.

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