Journal
SYNTHETIC COMMUNICATIONS
Volume 44, Issue 16, Pages 2344-2347Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2014.895014
Keywords
Alkoxyamine; alkyl bromide; O-alkylation
Categories
Funding
- NIDDK, National Institutes of Health
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The conventional route to alkoxyamine hydrochloride derivatives is by reaction of alkyl bromides with N-hydroxyphthalimide or N-hydroxysuccinimide followed by addition of hydrazine and HCl. Transformation of an alkyl bromide to the corresponding alkoxyamine hydrochloride can be accomplished more rapidly in good yields without using hazardous hydrazine by reaction of (Boc)(2)NOH (N,N'-di-tert-butoxycarbonylhydroxylamine) and alkyl bromide followed by addition of HCl. Alkoxyamine hydrochlorides are powerful reagents in organic synthesis that can be used to synthesize alkoxyimino derivatives after condensation with a ketone or aldehyde.
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