The Photochemical Behaviour of 5,5-Dimethyl-2(5H)-furanone

✍ Scribed by Elke Anklam; Paul Margaretha

• Publisher: John Wiley and Sons
• Year: 1983
• Tongue: German
• Weight: 433 KB
• Volume: 66
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19830660515

✦ Synopsis

Abstract

The photochemical behaviour of the title compound 2c was investigated in various solvents. In benzene and t‐butanol photodimerization affords the cis‐anti‐cis HH‐ and HT‐dimers (H = head, T = tail). In acetonitrile, cyclohexane and 2‐propanol, photoreduction competes with photodimerization. The photoreduction products are hydrodimers, solvent adducts and the saturated lactone (the 2H‐reduction product). In acetonitrile and cyclohexane H‐abstraction by the β‐C‐atom of the CC bond is the predominant reduction process. In 2‐propanol, solvent adducts to the α‐ and β‐C‐atoms are formed in equal amounts. In xanthone‐sensitized irradiations the ratio of HH‐ to HT‐dimer is the same as on direct irradiation and the relative rates of conversion of 2c to products in different solvents are also similar under both conditions.