O-Dealkylation s. Ethers

O-Dealkylation s. Ethers, cleavage, O-Detritylation N-Deallylation 32, 997 Deamination... 

N-Dealkylation, lactam ring closure with — 17, 898 O-Dealkylation (s. a. Ethers, cleavage)... 

The microsomal oxidations encountered include aliphatic side chain oxidations, aromatic hydroxylations, N-dealkylations, O- and S-dealkylations (which may also be viewed as ether cleavages), N-oxidations to N-oxides, and N-hydroxylations, and oxidation of divalent sulfur to sulfoxides. Representative examples are given in Table 3-1. 

The preferential dealkylation of a combined thio and 0-alkyl ether was selectively chemically achieved either at the O or the S atom by appropriate choice of reagent. Sodium iso-propylthiolate at 120°C added to 3-(methylthio)anisole in hexamethylphosphorictriamide in a nitrogen atmosphere followed after 2.5 hours by acidification gave 3-(methylthio)phenol in 88% yield, while sodium alone in hexamethylphosphorictriamide resulted in selective... 

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