Abstract
2,2,2-Trimethoxy-3,3-bis(trifluoromethyl)-2,2-dihydro-1,4,2-oxazaphosphol-4-enes on thermolysis undergo a 1,3-dipolar cycloreversion reaction with formation of bis(trifluoro-methyl) substituted nitrile ylides. Trapping reactions of the 1,3-dipolar species with α,β-unsaturated carboxylic acid esters and nitriles are described. 2-Aryl-3-carbethoxy-5,5-bis(trifluoromethyl)-1-pyrrolines obtained undergo an uncatalyzed autoxidation pro-cess to give 2-aryl-3-carbethoxy-3-hydroxy-5,5-bis(trifluoromethyl)-1-pyrrolines. 5,5-Di-fluoro-4-trifluoromethyl-2-oxazolines and 5-fluoro-4-trifluoromethyl-oxazoles formed as by-products indicate that the thermal induced [3+2]-cycloreversion reaction of 2,2,2-tri-methoxy-3,3-bis(trifluoromethyl)-2,2-dihydro-1,4,2-oxazaphosphol-4-enes is most likely a stepwise process.
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