An anomeric effect in photochemical hydrogen abstraction reactions of tetrahydropyranyl ethers | Zendy

Kim Hayday | Zendy; Ronald D. McKelvey | Zendy

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An anomeric effect in photochemical hydrogen abstraction reactions of tetrahydropyranyl ethers

Author(s) -

Kim Hayday,

Ronald D. McKelvey

Publication year - 1976

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo00874a037

Subject(s) - citation , altmetrics , abstraction , computer science , social media , anomer , information retrieval , world wide web , chemistry , philosophy , stereochemistry , epistemology

Hydrogen-atom abstraction from 2-methoxy-4-methyltetrahydropyran (1) by photochemically excited benzophenone in benzene gave methyl 3-methyl-5phenylvalerate and 3-methyl-6-valerolactone. The cis-isomer of 1 was 8.0 times as reactive as the trans-isomer, indicating that abstraction of an axial hydrogen atom is more favorable than abstraction of an equatorial hydrogen. This observation is rationalized in terms of antiperiplanar overlap of the carbon-hydrogen bond being broken with nonbonding orbitals on both oxygens. The two isomers of 1 did not interconvert during irradiation, indicating that the initial hydrogen abstraction is irreversible. An Anomeric Effect in Photochemical Hydrogen Abstraction Reactions of Tetrahydropyranyl Ethers 1

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