Bulletin of the Chemical Society of Japan p. 2374 - 2378 (1981)
Update date:2022-08-28
Topics:
Oae, Shigeru
Iida, Kazuyuki
Shinhama, Koichi
Takata, Toshikazu
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.
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