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The effect of electron withdrawing croups on the stability of thiabenzenes
Author(s) -
Pirelahi Hooshang,
Abdoh Yahyo,
Tavassoli Manoochehr
Publication year - 1977
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.5570140205
Subject(s) - chemistry , polar effect , sulfur , ring (chemistry) , medicinal chemistry , chemical stability , electron , stereochemistry , organic chemistry , physics , quantum mechanics
The reactions of p ‐trifluoromethylphenyllithium with 2,4,6‐triarylthiopyrylium perehlorates (Ar = Ph, p ‐CH 3 OC 6 H 4 , p ‐NMe 2 C 6 H 4 ) have been studied. The initially formed thiabenzenes were not slable enough to he isolated and rearranged readily to their corresponding 4‐( p ‐tri‐fluoromethylphenyl)‐2,4,6‐triarylthiopyrans. The instability of the intermediate thiabenzenes reveals that, in contrast to the stabilization effect of the electron‐withdrawing p ‐chloro‐ and pentalluorophcnyl groups attached to carbon atoms in sulfur ring, the electron‐withdrawing p ‐lrilluoromethyl group on subsliluenls attached to sulfur decreases the stability of thiabenzenes.