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The Reaction of 2,5‐Dimethoxy‐2,5‐Dihydrofuran with Dichloroketene
Author(s) -
Yang ChiaHsi,
Lin HuangChin,
Whang MawJohn
Publication year - 1986
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.198600019
Subject(s) - chemistry , tetrahydrofuran , cycloaddition , molecule , medicinal chemistry , stereochemistry , organic chemistry , catalysis , solvent
2,5‐Dimethoxy‐2,5‐dihydrofuran (DDF) reacts with dichloroketene to give 7,9‐dimethoxy‐3,3,5,5‐tetrachloro‐8‐oxabicyclo[4,3,0]‐noan‐2,4‐dione (I), and methyl chloro‐(2,5‐dihydro‐5‐methoxy‐2‐furanylidene) acetate (II). The reactions of 2,5‐dihydrofuran and 2,5‐dimethoxy‐tetrahydrofuran with dichloroketene were also‐studied for comparison. Compound II was derived from the insertion of a molecule of dichloroketene into the C‐O bond of DDF with subsequent dehydrochlorination. Compound I resulted from the cycloaddition of two molecules of dichloroketene to the C=C bond of DDF. A mechanism involving a 1,5‐dipolar intermediate is proposed to account for this novel reaction.