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

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 ?-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.

SUBMITTER: Hirose D

PROVIDER: S-EPMC3778400 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Hirose Daisuke D Taniguchi Tsuyoshi T

Beilstein journal of organic chemistry 20130820

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. ...[more]

PMID: 24062832

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