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Organische photochemie XXI. 9 H ‐cyclopenta[ b ] [1]benzoselenin ‐ein neues heterocydisches ringsystem
Author(s) -
Praefcke Klaus,
Schmidt Dietmar
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160110
Subject(s) - chemistry , intramolecular force , derivative (finance) , ring (chemistry) , medicinal chemistry , aryl , stereochemistry , organic chemistry , alkyl , financial economics , economics
By way of a photo‐induced selenolester‐seleninone rearrangement, the derivative 5 of a new heterocyclic ring system, 9 H ‐cyclopenta[ b ][1]benzoselenin, has been formed. This rearrangement occurs via a new photosubstitution reaction of S ‐aryl‐ in competition with Se ‐aryl‐groups, followed by photocyclization using 2‐p ‐tolythiocyclopentene ‐1 ‐ selenocarbonic acid Se‐p‐ tolylester (1a) as starting materials. As a competing product in this photo‐rearrangement, a second heterocycle, 7‐methylcyclopenta[ b ] [1]benzothiopyrone (4) (9) has been formed via an intramolecular photochemical Friedel Crafts reaction.