The tertiary alcohol (I) does not yield the normal Barbier-Wieland degradation product ( 11), but the acid (111) and the quinone (IV). The related tertiary alcohol (VI) gives a small yield of the expected acid (IX) and a little acetophenone, but the major reaction product is the ketone (VIII).
Bromoallenes give allenic carbenes under basic conditions, which react with methylindoles to give alkenylquinolines by ring expansion and alkynyl-and allenyl-3H-indoles. Under the same conditions 2.5-dimethylpyrrole is converted into a 3-al kenyl-2,6-dimethylpyridine.
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