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Studies on silyl furans. II . Halodesilylation of 2‐trimethylsilyl‐3,4‐bis(methoxycarbonyl)furans
Author(s) -
Nakayama Koukji,
Harigaya Yoshiharu,
Okamoto Hiroshi,
Tanaka Akira
Publication year - 1991
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.5570280404
Subject(s) - chemistry , iodine monochloride , bromine , furan , trimethylsilyl , yield (engineering) , medicinal chemistry , sulfuryl chloride , silylation , acetonitrile , carbon tetrachloride , halogenation , organic chemistry , iodine , catalysis , materials science , metallurgy
Reactions of 2‐trimethylsilyl‐3,4‐bis(methoxycarbonyl)furans 1a,b with sulfuryl chloride, bromine, and iodine monochloride in acetonitrile afforded the corresponding 2‐halo‐3,4‐bis(methoxycarbonyl)furans 2a‐f via chloro‐, bromo‐, and iododesilylation in good yields, respectively. However, the reaction of 1a with bromine in carbon tetrachloride mainly gave 2‐bromo‐ 2b and 2‐bromo‐5‐trimethylsilyl‐3,4‐bis(methoxycarbonyl)furan ( 3 ) in 37% and 45% yields. Similarly, the reaction of 1a with iodine monochloride afforded 1a , 2‐chloro‐ 2a and 2‐iodo‐3,4‐bis(methoxycarbonyl)furan ( 2c ) in 50%, 27%, and 23% yield.