Geranyl phenyl sulfone

Allylic sulfones undergo the same reaction, as formulated for the conversion of geranyl phenyl sulfone (4) into 5.1... 

Oxidation of sulfur and phosphorus compounds. The peroxide has been used to oxidize the sulfide (2) to the corresponding sulfone in 83% yield without attack of the double bond. Geranyl phenyl sulfide is oxidized to the corresponding sulfone in Ninular yield.4 Trialkylphosphines and phosphites are oxidized to the corresponding oxides in high yield.5... 

In the 1980s, the Japanese firm Kuraray developed a stereoselective Vitamin A synthesis, which follows the Cm + Cm concept. The synthetic building blocks are cyclogeranyl phenyl sulfone and a Cm-aldehyde, which is obtainable by allylic oxidation of geranyl acetate with t-butyl hydroperoxide. [81] The alcohol function is protected as the THP-ether, and the sulfmic acid and hydroxytetrahydro-pyran are eliminated with potassium fbutoxide in petroleum ether. By means of this double elimination, the reduction step is avoided. 

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