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Air-Water Interface Effects on the Regioselectivity of Singlet Oxygenations of a Trisubstituted Alkene.

ABSTRACT: The regioselective synthesis of allylic hydroperoxide sulfonates by singlet oxygenation at the air-water interface has been found to depend on the concentration of the alkene sulfonate and added calcium salt. The regioselectivity is proposed to originate from an orthogonal alkene relative to the water surface for preferential methyl hydrogen abstraction by airborne singlet oxygen in an ene reaction. The findings hint that the air-water interface is a locale for synthetic reactions.

SUBMITTER: Malek B 

PROVIDER: S-EPMC4832427 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Air-Water Interface Effects on the Regioselectivity of Singlet Oxygenations of a Trisubstituted Alkene.

Malek Belaid B   Ghogare Ashwini A AA   Choudhury Rajib R   Greer Alexander A  

Tetrahedron letters 20150701 30

The regioselective synthesis of allylic hydroperoxide sulfonates by singlet oxygenation at the air-water interface has been found to depend on the concentration of the alkene sulfonate and added calcium salt. The regioselectivity is proposed to originate from an orthogonal alkene relative to the water surface for preferential methyl hydrogen abstraction by airborne singlet oxygen in an ene reaction. The findings hint that the air-water interface is a locale for synthetic reactions. ...[more]

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