Photosolvolysis of 2‐Allylated Anilines to 2‐Indanols | Zendy

Scholl Bernhard | Zendy; Jolidon Synèse | Zendy; Hansen HansJürgen | Zendy

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Photosolvolysis of 2‐Allylated Anilines to 2‐Indanols

Author(s) -

Scholl Bernhard,

Jolidon Synèse,

Hansen HansJürgen

Publication year - 1986

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19860690122

Subject(s) - chemistry , yield (engineering) , medicinal chemistry , intramolecular force , cycloaddition , benzene , irradiation , dimethylaniline , stereochemistry , photochemistry , organic chemistry , catalysis , materials science , physics , nuclear physics , metallurgy

It is shown that 2‐allylated anilines ( cf. Schemes 2–4, 7 , and 8 ) on irradiation in protic solvents such as H 2 O. MeOH, and EtOH in the presence of H 2 SO 4 undergo a novel photosolvolysis reaction to yield specifically trans ‐2‐hydroxy‐ and trans ‐2‐alkoxy‐1‐methylindanes. Intermediates are presumably tricyclo[4.3.0.0 1,8 ]nona‐2,4‐dienes formed in an intramolecular [2 s + 2 s ] 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 H 2 SO 4 /MeOH the ammonium group reductively to yield (1‐methylallyl)benzene ( 19 ) and 1‐methylindane ( 20 ), respectively.

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