✦ LIBER ✦
Novel solvent hydrogen-bonding effects in the singlet oxygen ene reaction: a comparison of α,β-unsaturated esters and acids
✍ Scribed by Kristina L Stensaas; Jason A Payne; Alexa N Ivancic; Anisha Bajaj
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 65 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The photooxidations of tiglic acid, angelic acid, 2,3-dimethyl-2-butenoic acid and their corresponding methyl esters using singlet oxygen were investigated in methanol and methanol/water solvent mixtures and compared to non-hydrogen-bonding solvents with different dielectric constants. The major and minor ene allylic hydroperoxide products were quantified and this ratio for the acids was found to be dependent on a hydrogen-bonding interaction between the solvent and substrate.