75615-02-0Relevant articles and documents
Hydrosulfite Reduction of N-Nitroso-1,2,3,4-tetrahydroisoquinolines and Oxidation of N-Amino-1,2,3,4-tetrahydroisoquinolines
Powell, Burwell F.,Overberger, C. G.,Anselme, J.-P.
, p. 121 - 128 (2007/10/02)
The sodium hydrosulfite reduction of N-nitroso-1,2,3,4,-tetrahydroisoquinolines (5) does not result in the loss of nitrogen and leads to the corresponding hydrazine 6 which upon oxidation with mercuric oxide in ethanol at 62 deg gives the hexahydrotetrazine 7 in 39percent yield.Treatment of the n-tosyl derivative of 6 with base affords 7 in nearly quantitative yield.Oxidation of 6 in 1-butanol at 95 deg results in the formation of a complex product mixture from which only one component, 1,1'-azobis-3,4-dihydroisoquinoline (8) could be isolated.Surprisingly the sodium hydrosulfite reduction of 2-nitroso-3-phenyl-1,2,3,4-tetrahydroisoquinoline (15) also failed to proceed with loss of nitrogen and yields the corresponding hydrazine 16.However, 16 was cleanly oxidized by mercuric oxide in ethanol at 62 deg with concurrent elimination of nitrogen to afford 2-phenylindane in 75percent yield.Possible rationalizations for these results are presented.
