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2004
Aminomethylation
O 0271
Dibromomethane as One-Carbon Source in Organic Synthesis: The Mannich
Formation from the Reaction of Phenolic Compounds with a Preheated Mix44- 061 Base
ture of Dibromomethane and Diethylamine. — A preheated mixture of CH2Br2 and
Et2NH proves to be a convenient and economic reagent for the synthesis of Mannich
bases [cf. (IV), (VI)] from corresponding aryl alcohols. At higher reaction temperatures, elimination of Et2NH from Mannich base can occur leading to bis-arylmethane
derivatives such as (VII). An oxazine (IX) is obtained using allylamine instead of
Et2NH due to a cyclization. — (HON*, Y.-S.; CHOU, Y.-Y.; WU, I.--.; Synth.
Commun. 34 (2004) 12, 2253-2267; Dep. Chem. Biochem., Natl. Chung-Cheng Univ.,
Chia-Yi 621, Taiwan; Eng.) — R. Staver
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