A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under Mild Conditions

A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under Mild Conditions

A samarium-promoted synthesis of (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols in high yields and with total selectivity is reported. This reaction together with the easy and efficient preparation of the 1-bromo-1-nitroalkan-2-ols constitutes a simple and advantageous alternative toward nitroalke...

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Veröffentlicht in:Journal of organic chemistry 2007-07, Vol.72 (14), p.5421-5423
Hauptverfasser: Concellón, José M, Bernad, Pablo L, Rodríguez-Solla, Humberto, Concellón, Carmen
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Zusammenfassung:A samarium-promoted synthesis of (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols in high yields and with total selectivity is reported. This reaction together with the easy and efficient preparation of the 1-bromo-1-nitroalkan-2-ols constitutes a simple and advantageous alternative toward nitroalkenes with total E-stereoselectivity. A mechanism is proposed to explain the E-stereoselectivity of the β-elimination reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0706271