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Experimental study on the reaction pathway of α‐haloacetophenones with nucleophiles: direct substitution or carbonyl addition ?
Author(s) -
Katayama Mika,
Sasagawa Keita,
Yamataka Hiroshi
Publication year - 2012
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.2901
Subject(s) - chemistry , substituent , reactivity (psychology) , ether , alcohol , medicinal chemistry , dimer , substitution reaction , nucleophilic substitution , nucleophile , hydrolysis , organic chemistry , catalysis , medicine , alternative medicine , pathology
The reaction of PhCOCH 2 Cl with OH – gave the expected α‐substituted alcohol (PhCOCH 2 OH) in addition to three dimer products. To clarify whether the substitution product is formed by direct S N 2 or via carbonyl addition , the reaction of PhCOCH 2 Cl and OMe – was examined. The reaction gave two products, PhCOCH 2 OH as the major product after acid hydrolysis and PhCOCH 2 OMe as the minor product. An electron‐withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was concluded that the alcohol was formed via carbonyl addition‐epoxidation route, whereas the ether was formed by the direct substitution route. Copyright © 2012 John Wiley & Sons, Ltd.