Oxone/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro- and [beta]-Iodonitro-Substituted Alkenes

Oxone (2KHSO5·KHSO4·K2SO4) was used to promote the nitration of alkenes and alkynes with sodium nitrite (NaNO2) and potassium iodide (KI). This stable, easy-to-handle, and environmentally benign oxidant was used under mild conditions (room temperature) and provided short reaction times. Styrene deri...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-11, Vol.2014 (33), p.7433
Main Authors: Hlekhlai, Sornsiri, Samakkanad, Natthapol, Sawangphon, Tassaporn, Pohmakotr, Manat, Reutrakul, Vichai, Soorukram, Darunee, Jaipetch, Thaworn, Kuhakarn, Chutima
Format: Article
Language:English
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Summary:Oxone (2KHSO5·KHSO4·K2SO4) was used to promote the nitration of alkenes and alkynes with sodium nitrite (NaNO2) and potassium iodide (KI). This stable, easy-to-handle, and environmentally benign oxidant was used under mild conditions (room temperature) and provided short reaction times. Styrene derivatives that did not contain electron-donating groups afforded the corresponding nitro alkenes in moderate to good yields, whereas aliphatic alkenes and electron-deficient alkenes were not good substrates. Under similar reaction conditions, aryl alkynes yielded [beta]-iodonitro alkenes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402750