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Cleavage of 1,3-dithianes via acid-catalyzed hydrolysis of the corresponding 1,3-dithianemonooxides.

  作者 Krohn, Karsten;Cludius-Brandt, Stephan;  
  选自 期刊  Synthesis;  卷期  2008年-15;  页码  2369-2372  
  关联知识点  
 

[摘要]The hydrolysis of 1,3-dithianes to their parent carbonyl compds. via their corresponding monosulfoxides was systematically investigated. The oxidn. of the 1,3-dithianes was carried out in high yields using tert-Bu hydroperoxide. Acid-catalyzed hydrolysis of the monosulfoxides to the carbonyl compds. was then performed in excellent yields. The cleavage reactions were monitored by gas chromatog. and kinetics were investigated on substrates varying in electron d. and steric requirements. Neither effect prevented high overall yields in the cleavage reaction.

 
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