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Air–water interface effects on the regioselectivity of singlet oxygenations of a trisubstituted alkene

Author:
Malek, Belaid, Ghogare, Ashwini A., Choudhury, Rajib, Greer, Alexander
Source:
Tetrahedron letters 2015 v.56 no.30 pp. 4505-4508
ISSN:
0040-4039
Subject:
calcium, chemical reactions, chemical structure, hydrogen, liquid-air interface, regioselectivity, singlet oxygen, sulfonates
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.
Agid:
6040288