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Synlett 2001; 2001(Special Issue): 1003-1005
DOI: 10.1055/s-2001-14646
DOI: 10.1055/s-2001-14646
letter
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Convenient Procedure for One-pot Conversion of Azides to N-Monomethylamines
Further Information
Publication History
Publication Date:
31 December 2001 (online)
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One-pot conversion of azides to N-monomethylamines is described. Two optional protocols have been developed, which share the first stage, the reaction of an azide with (CH3)3P to generate the corresponding iminophosphorane. This Staudinger intermediate, thus generated, is either methylated with CH3I and hydrolyzed (method A), or treated with (HCHO) n and reduced with NaBH4 (method B), thereby giving the corresponding N-monomethylamine in high yield.
azides - N-monomethylamines - Staudinger reaction - iminophosphorane - aza-Wittig reaction