SYNTHESIS OF 5-IODOBENZOFURANS AND 6-IODOBENZOPYRANS VIA DIRECT IODINATION WITH MERCURY(II) OXIDE-IODINE REAGENT

Authors
ORITO K HATAKEYAMA T TAKEO M SUGINOME H TOKUDA M
Citation
K. Orito et al., SYNTHESIS OF 5-IODOBENZOFURANS AND 6-IODOBENZOPYRANS VIA DIRECT IODINATION WITH MERCURY(II) OXIDE-IODINE REAGENT, Synthesis, (1), 1997, pp. 23
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
1
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):1<23:SO5A6V>2.0.ZU;2-7
Abstract
A tin(IV) chloride assisted iodo-cyclization of 2-allylphenol gave 2-i odomethyl-2,3-dihydrobenzofuran. A similar cyclization of 2-crotylphen ol gave 3-iodo-2-methyl-3,4-dihydro-2H-benzopyran, exclusively. By iod ination with mercury(II) oxide-iodine reagent in dichloromethane, 2,3- dihydrobenzofurans or 3,4-dihydro-2H-benzopyrans including the above b enzocyclic ethers were easily converted to the corresponding 5- or 6-i odo derivatives, regioselectively, in good yield.