Facile and efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.
Isolation of the quinone mono O,S-acetal intermediates of the aromatic pummerer-type rearrangement of p-sulfinylphenols with 1-ethoxyvinyl esters
A versatile synthetic building block and evidence for the mechanism of the Pummerer-type rearrangement have been obtained in the form of the acetal intermediate B, isolated in the reaction of p-sulfinylphenols 1 to p-quinones 2 induced by acid anhydrides. Thus, a method is now also available for the efficient preparation of quinone monoacetals under nonoxidative conditions.
Kita,Takeda,Matsugi,Iio,Gotanda,Murata,Akai
p. 1529 - 1531
(2007/10/03)
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