The Pschorr Cyclization of Aromatic Amines with t-Butyl Thionitrate in Nonaqueous Media

Article abstract of DOI:10.1246/bcsj.54.2374

The Pschorr cyclization of various arylamines with t-butyl thionitrate under nonaqueous conditions gave the corresponding cyclic products in moderate yields.The same reaction was also found to proceed readily with p-toluenesulfonyl nitrite at room tempoerature.Treatment of o-aminophenyl allyl ether or sulfide with t-butyl thionitrate resulted in the intramolecular Meerwein arylation to the olefinic bond affording 3-chlorochroman or - thiochroman, through the yield was low.The plausible mechanism of the Pschorr cyclization with t-butyl thionitrate is discussed.