Helvetica Chimica Acta p. 184 - 194 (1986)
Update date:2022-08-05
Topics:
Scholl, Bernhard
Jolidon, Synese
Hansen, Hans-Juergen
It is shown that 2-allylated anilines (cf.Schemes 2-4,7, and 8) on irradiation in protic solvents such as H2O.MeOH, and EtOH in the presence of H2SO4 undergo a novel photosolvolysis reaction to yield specifically trans-2-hydroxy- and trans-2-alkoxy-1-methylindanes.Intermediates are presumably tricyclo<4.3.0.01,8>nona-2,4-dienes formed in an intramolecular <2s+2s> cycloaddition reaction (cf.Scheme 7).On the other hand, N,N,N-trimethyl-2-(1'-methylallyl)anilinium salts 18 (Scheme 6) and 2-(3'-butenyl)-N,N-dimethylaniline (17) lose on irradiation in MeOH or H2SO4/MeOH the ammonium group reductively to yield (1-methylallyl)benzene (19) and 1-methylindane (20), respectively.
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