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Literature DB >> 27092011

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

Belaid Malek¹, Ashwini A Ghogare¹, Rajib Choudhury¹, Alexander Greer¹.

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.

Entities: Chemical Gene

Keywords: airborne singlet oxygen; alkene sulfonate; ene reaction; phase-separation; selectivity

Year: 2015 PMID： 27092011 PMCID： PMC4832427 DOI： 10.1016/j.tetlet.2015.05.111

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

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References

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

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