166327-08-8Relevant academic research and scientific papers
Neighbouring Group Effects in a Pummerer-Type Rearrangement: A Facile Entry into 3,1-Benzoxathiins
Kersey, Ian D.,Fishwick, Colin W. G.,Findlay, John B. C.,Ward, Peter
, p. 6819 - 6834 (2007/10/02)
Arylmethyl sulphoxides treated with trialkylsilyl halide and base undergo a Pummerer-type rearrangement to give α-siloxy and α-chlorosulphides.However, the presence of an ortho hydroxymethyl group results in the exclusive and efficient formation of the α-chlorosulphides, presumably mediated via an intramolecular attack to yield an alkoxysulphonium salt.These 2-(hydroxymethyl)aryl chloromethylsulphides can then be converted into the corresponding 3,1-benzoxathiins via an intramolecular cyclisation.Preliminary investigation of the chemistry of these 3,1-benzoxathiins, reveals that in one case, a novel base induced ring contraction occurs to yield a benzothiophene.
