Beilstein Journal of Organic Chemistry 2013-01-01

Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water.

Daisuke Hirose, Tsuyoshi Taniguchi

Index: Beilstein J. Org. Chem. 9 , 1713-7, (2013)

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Abstract

Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp(3) C-H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.