NEW, FACILE SYNTHESIS OF 3,3-DISUBSTITUTED PHTHALIDES BASED ON THE REACTION OF alpha-SUBSTITUTED 2-LITHIOSTYRENES WITH CARBON DIOXIDE

A new method to prepare 3,3-disubstituted phthalides [isobenzofuran-1(3H)-ones] from alpha-substituted 2-bromostyrenes has been developed. The reaction of alpha-substituted 2-lithiostyrenes, generated in situ by bromine-lithium exchange between alpha-substituted 2-bromostyrenes and butyllithium, wit...

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Bibliographic Details
Published inHeterocycles Vol. 81; no. 1; pp. 163 - 169
Main Authors Kobayashi, Kazuhiro, Kozuki, Taketoshi, Fukamachi, Shuhei, Konishi, Hisatoshi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Phthalide
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
CHIRAL PHTHALIDES
MICROWAVE
FRIEDEL-CRAFTS REACTIONS
METHYL
IODINE
Isobenzofuran-1(3H)-one
Carbon Dioxide
2-Lithiostyrene
Lactonization
DERIVATIVES
CYCLIZATION
ISOBENZOFURAN-1(3H)-ONES
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Summary:A new method to prepare 3,3-disubstituted phthalides [isobenzofuran-1(3H)-ones] from alpha-substituted 2-bromostyrenes has been developed. The reaction of alpha-substituted 2-lithiostyrenes, generated in situ by bromine-lithium exchange between alpha-substituted 2-bromostyrenes and butyllithium, with carbon dioxide gave the corresponding lithium 2-vinylbenzoates, which upon treatment with concentrated hydrochloric acid afforded the desired products in one pot.
ISSN:0385-5414
DOI:10.3987/COM-09-11837