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Studies on the reaction of organotin phenoxides with ethyl propiolate catalysed by triethylamine and tin(IV) chloride
Author(s) -
Kinart Wojciech J.,
Kinart Andrzej
Publication year - 2007
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1216
Subject(s) - chemistry , triethylamine , tin , chloride , hydrolysis , organic chemistry , medicinal chemistry , ethyl benzoate , nuclear chemistry , catalysis
Different tributyltin phenoxides react at room temperature with ethyl propiolate in benzene, in the presence of tin(IV) chloride, triethylamine and their mixture to give the derivatives of 3‐phenoxyacrylic acid ethyl ester. Exceptionally, 3‐(2‐hydroxyphenyl)acrylic acid ethyl ester and 3‐(2‐hydroxy‐5‐methylphenyl)acrylic acid ethyl ester have been obtained from the reaction of tributylphenoxytin and tributyl( p ‐tolyloxy)tin, respectively catalysed by SnCl 4 , and they have been easily hydrolysed to coumarin and 6‐methylcoumarin. Copyright © 2007 John Wiley & Sons, Ltd.