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Oxidation of Alcohols to Aldehydes or Ketones with 1‐Acetoxy‐1,2‐benziodoxole‐3(1 H )‐one Derivatives
Author(s) -
Iinuma Masataka,
Moriyama Katsuhiko,
Togo Hideo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301466
Subject(s) - chemistry , reagent , iodine , organic chemistry , alcohol oxidation , alcohol , reusability , ketone , medicinal chemistry , software , computer science , programming language
Various benzylic and aliphatic alcohols were smoothly oxidized to the corresponding aromatic aldehydes and ketones as well as aliphatic ketones by treatment with 1‐acetoxy‐5‐nitro‐1,2‐benziodoxole‐3(1 H )‐one ( ANBX ), 1‐acetoxy‐5‐bromo‐1,2‐benziodoxole‐3(1 H )‐one ( ABBX ), 1‐acetoxy‐5‐chloro‐1,2‐benziodoxole‐3(1 H )‐one ( ACBX ), and 1‐acetoxy‐5‐fluoro‐1,2‐benziodoxole‐3(1 H )‐one ( AFBX ). These new trivalent iodine compounds were prepared from 5‐substituted 2‐iodobenzoic acids and meta ‐chloroperoxybenzoic acid ( m ‐CPBA). ANBX and ABBX were the most effective reagents for this oxidation of alcohols, and this present reaction is very attractive because of the ease of product isolation and the reusability of the reagents.