Formation of unsaturated esters in the single electron transfer reaction of cyclopropanone acetals with quinones under non-irradiated conditions
✍ Scribed by Manabu Abe; Akira Oku
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 254 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
While a number of cyclopropane derivatives, which have been regarded to have higher oxidation potentials than akane homologues. have been investigated in search of their electron transfer ptofile.l-5) the reactions were examined mainly under photolysis conditions. Among them, scarcely investigated cyclopropanone ~cetals 1 and hemiacetals 2 6) seem to us as promising donors in combination with appropriate acceptors at their ground states because of two oxygenic substituents.7) In this respect, we report here the intervention of a single electron transfer (SET) reaction mechanism in the non-irradiated reactions of acetals 1 and 2 with 2,3-dichloro-5,6dicyano-p-benzoquinone (DDQ) or 2,3.5,6-tetrachloro-p-benzquinone (chloranil), where the intenfention of C-Q and C-C bonded adducts were clearly demonstrated. Also found was that structural variations in both donor and acceptor determine the overall maction pathway.