Experimental Study on the Reaction Pathway of α-Haloacetophenones with NaOMe: Examination of Bifurcation Mechanism

…, K Sasagawa, K Wakisaka, S Monjiyama…

Index: Tagawa, Kohei; Sasagawa, Keita; Wakisaka, Ken; Monjiyama, Shunsuke; Katayama, Mika; Yamataka, Hiroshi Bulletin of the Chemical Society of Japan, 2014 , vol. 87, # 1 p. 119 - 126

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Abstract

The reaction of PhCOCH 2 Br and NaOMe in MeOH gave PhCOCH 2 OH as the major product and PhCOCH 2 OMe as the minor product. Substituent effects on the reactivity and product selectivity revealed that an electron-withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was indicated that the alcohol was formed via carbonyl addition-epoxidation, whereas the ether was formed by ...

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