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Unexpected Metal‐Free Transformation of gem ‐Dibromomethylenes to Ketones under Acetylation Conditions
Author(s) -
Kimura Rino,
Sawayama Yusuke,
Nakazaki Atsuo,
Miyamoto Kazunori,
Uchiyama Masanobu,
Nishikawa Toshio
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403277
Subject(s) - triethylamine , acetic anhydride , dichloromethane , acetylation , transformation (genetics) , chemistry , atmosphere (unit) , metal , organic chemistry , medicinal chemistry , catalysis , thermodynamics , biochemistry , physics , solvent , gene
Novel conditions for the transformation of gem ‐dibromomethylenes to ketones are described. gem ‐Dibromo compounds were treated with acetic anhydride and triethylamine in dichloromethane/water at room temperature under an air atmosphere to give the corresponding ketones in moderate yields. A radical mechanism is proposed based on experimental results.