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Cleavage of (–)‐Eschscholtzine with Sodium in Liquid Ammonia
Author(s) -
Lee ShoeiSheng,
Lin ChiaYin,
Chen ChungHsiung
Publication year - 1991
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199100066
Subject(s) - chemistry , liquid ammonia , cleavage (geology) , regioselectivity , ammonia , yield (engineering) , sodium , medicinal chemistry , organic chemistry , catalysis , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
(–)‐Eschscholtzine was cleaved with sodium in liquid ammonia to yield 2,8‐dihydroxy‐ N ‐methylpavine and 2,9‐dihydroxy‐ N ‐methylpavine. This reaction indicates regioselectivity by cleavage mainly at a site para to the methine carbon of a bridgehead.
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