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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 .