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Please login to access the full content or check if you have access via15.5.1.2.1.8 Variation 8: From an N-Sulfonyl-1,2,3,4-tetrahydroisoquinoline
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Álvarez, M.; Joule, J. A., Science of Synthesis, (2005) 15, 735.
In a special situation where the tetrahydroisoquinoline has been synthesized in such a way as to leave an arylsulfonyl group on the nitrogen, a 1,2-elimination of arenesulfinate can be induced by base, obviously most easily if there is a function at C1 (ester in the known examples) to acidify the C1-hydrogen (Scheme 120).[69] Mixtures of 3,4-dihydro- and fully aromatized isoquinolines, e.g. 267 and 268, are obtained. There do not seem to be any examples in which an arylsulfonyl group is added to a preformed 1,2,3,4-tetrahydroisoquinoline in order to achieve aromatization.
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References
| [69] | Meeee, M.; Meeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
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