Publication: Oxone<sup>®</sup>/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro- and β-Iodonitro-Substituted Alkenes
Issued Date
2014-11-01
Resource Type
ISSN
10990690
1434193X
1434193X
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2-s2.0-84942001936
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Mahidol University
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SCOPUS
Bibliographic Citation
European Journal of Organic Chemistry. Vol.2014, No.33 (2014), 7433-7442
Suggested Citation
Sornsiri Hlekhlai, Natthapol Samakkanad, Tassaporn Sawangphon, Manat Pohmakotr, Vichai Reutrakul, Darunee Soorukram, Thaworn Jaipetch, Chutima Kuhakarn Oxone<sup>®</sup>/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro- and β-Iodonitro-Substituted Alkenes. European Journal of Organic Chemistry. Vol.2014, No.33 (2014), 7433-7442. doi:10.1002/ejoc.201402750 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/33610
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Title
Oxone<sup>®</sup>/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro- and β-Iodonitro-Substituted Alkenes
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Abstract
© Copyright 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 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 β-iodonitro alkenes. Oxone® (2KHSO5·KHSO4·K2SO4) was used to promote the reactions of alkenes and alkynes with sodium nitrite (NaNO2) and potassium iodide (KI) to afford the corresponding nitro and β-iodonitro-substituted alkenes, respectively, in moderate to good yields.