The synthesis of 1,2,5,6-dibenzo-9-oxa-[3.3.1]-bicyclonona-2,6-diene, a novel reaction of phenylacetaldehyde in fluorosulfonic acid.
β Scribed by Jacques Kagan; Shi-Yan Chen; Dalmacio A. Agdeppa Jr.; William H. Watson; Volker Zabel
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 116 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
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AbstractΓHighly enantio-and diastereo-selective synthesis of C 2 -symmetric 9-oxabicyclo[3.3.1]nona-2,6-diene and the corresponding C 2 -symmetric 2,3,6,7-tetrol has been achieved starting from optically active 5-cyclooctene-1,2-diol prepared by an enzymatic procedure.
Treatment of 5-(2-hydroxyaryl)thianthreniumyl perchlorates 1 with sodium hydride in tetrahydrofuran at reflux gave the title compounds 5 in excellent yields. For the reactivities of the compounds 5, the selected compounds 5 were subjected under the conditions of electrophilic substitution reactions.