The effect of electron withdrawing croups on the stability of thiabenzenes | Zendy

Pirelahi Hooshang | Zendy; Abdoh Yahyo | Zendy; Tavassoli Manoochehr | Zendy

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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.

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