Oxidative Nitration of Alkenes with tert-Butyl Nitrite and Oxygen

• Published in: Advanced synthesis & catalysis Vol. 353; no. 14-15; pp. 2643 - 2647
• Main Authors: Taniguchi, Tsuyoshi, Yajima, Atsushi, Ishibashi, Hiroyuki
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.10.2011; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Alkenes; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Derivatives; Exact sciences and technology; Free radicals chemistry; Nitrates; Nitration; Nitrites; Nitro compounds; Organic chemistry; oxygenation; Physical Sciences; radical reactions; Reactivity and mechanisms; Science & Technology; Synthesis; ALKYL NITRITES; ACID; AUTOXIDATION; CONVERSION; SIDE-CHAIN; CONJUGATED DIENES; radical reactions; oxygenation; nitrites; alkenes; AROMATIC-COMPOUNDS; AQUEOUS-SOLUTION; nitration; DERIVATIVES; NITROGEN-DIOXIDE; Nitration; Alkene; Oxidation; Oxygenation; Free radical reaction; Ethylenic compound; Organic nitrite
• ISSN: 1615-4150; 1615-4169; 1615-4169
• DOI: 10.1002/adsc.201100315

A method for the oxidative nitration of alkenes using a combination of tert‐butyl nitrite and molecular oxygen to give β‐nitro alcohols and their nitrate derivatives has been developed. The present reaction provides a practical method for the synthesis of nitro compounds because of the mild reaction conditions, the use of inexpensive reagents and a simple experimental procedure.