Magnesium nitride as a convenient source of ammonia: Preparation of primary amides

Organic Letters

Volumn 10, Issue 16, 2008, Pages 3623-3625

  Veitch, Gemma E ^a   Bridgwood, Katy L ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMMONIA; ESTER; MAGNESIUM DERIVATIVE; MAGNESIUM NITRIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMIDES; AMMONIA; ESTERS; MAGNESIUM COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 54049141740     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801398z     Document Type: Article

References (15)

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9. A Beilstein search displayed 1226 hits for natural products containing primary amides.
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13. Sigma-Aldrich catalog no. 341428.
14. In an attempt to recreate the reaction medium generated with magnesium nitride, cyclohexane methyl ester 1 was treated with 2 M ammonia in methanol and additional magnesium methoxide. However, the desired amide 2 was still isolated in low yield (23%). Further studies are currently underway to ascertain the precise mechanism of action of this reagent.
15. See the Supporting Information for full experimental details.