Regioselectivity Control of the Ring Opening of Epoxides With Sodium Azide in a Microreactor

Rajesh Munirathinam, Daejune Joe, Jurriaan Huskens, Willem Verboom

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11 Citations (Scopus)
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The reaction of different types of aromatic and aliphatic epoxides with sodium azide to give vicinal azido alcohols was studied in a microreactor with and without pillars in the channels. Dependent on the substrate, the regioselectivity of the ring opening is affected by the used solvent system, viz. acetonitrile–water (sometimes with 10% acetic acid to promote the reactivity of substrates) or t-butyl acetate–water containing Tween80 as a surfactant. For styrene oxide and α-methylstyrene oxide, the α/ß regioselectivity changes from 4 to 10 and 1.7 to 6.2, respectively, going from acetonitrile–water to Tween80-containing t-butyl acetate–water. The addition of a surfactant (Tween80) stabilizes the interface in the biphasic t-butyl acetate–water. Pillar-containing microreactors gave better conversions than microreactors without pillars and lab scale reactions, probably due to better mixing.
Original languageEnglish
Pages (from-to)129-134
JournalJournal of flow chemistry
Issue number4
Publication statusPublished - 2012


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