Addition reactions of thiophenols with dihydro‐ and tetrahydropyridinecarbonitriles. A comparison with reactions of phenols | Zendy

Butt Graeme L. | Zendy; Deady Leslie W. | Zendy

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Addition reactions of thiophenols with dihydro‐ and tetrahydropyridinecarbonitriles. A comparison with reactions of phenols

Author(s) -

Butt Graeme L.,

Deady Leslie W.

Publication year - 1984

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.5570210411

Subject(s) - chemistry , phenols , derivative (finance) , medicinal chemistry , organic chemistry , stereochemistry , economics , financial economics

p ‐Chlorothiophenol reacts with 1‐methyl‐1,2,5,6‐tetrahydropyridine‐X‐carbonitriles ( 1 , X = 4, 6 , X = 3) and with 1‐methyl‐1,Y‐dihydropyridine‐3‐carbonitrile (7, Y = 6, 8 , Y = 4) to give the anticipated addition products. Geometric isomers were formed from 6 , but not from 1 , and the stereochemistry of the products has been determined. The chemistry of the reactions with p ‐cresol was quite different. No reaction occurred with 6 or 7 , while 8 gave a 6‐(2‐hydroxy‐5‐methylphenyl)‐ derivative, analogous to the unexpected product obtained previously from 1 .

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