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

Beilstein journal of organic chemistry (2013-09-26)
Daisuke Hirose, Tsuyoshi Taniguchi
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
tert-Butyl nitrite, 90%

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