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Nucleophilic vinylic substitution of halocoumarins and halo‐l,4‐naphthoquinones with morpholine
Author(s) -
Oh Changsok,
Yi Inwoo,
Park Kyong Pae
Publication year - 1994
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.5570310426
Subject(s) - chemistry , morpholine , nucleophile , yield (engineering) , halogen , nucleophilic substitution , vicinal , medicinal chemistry , substitution reaction , deuterium , organic chemistry , carbon atom , ring (chemistry) , catalysis , materials science , alkyl , metallurgy , physics , quantum mechanics
Reactions of morpholine with 4‐halocoumarins 1 , 3‐halocoumarins 3 , and 2‐halo‐l,4‐naphthoquinones 8 yield two different products, one where halogen is replaced by a nucleophile at the same carbon and the other where the nucleophile is attached to the vicinal carbon away from that bearing the halogen. It is considered that reactions proceeds through nucleophilic vinylic substitution by comparision of the reaction products and deuterium exchange experiments. Plausible mechanisms for these routes are suggested.