The Ozonolysis of α-Terpineol - Unusual Formation of a 6,6-Dimethylfulvene Epoxide
Ozonolysis of α-terpineol (1) followed by steam distillation in the presence of acid is known to give 4-isopropylidenecyclopentenyl methyl ketone (3). In the absence of light, the latter is oxidized by air to the 4-(1-hydroperoxy-1-methylethyl)-1,3-cyclopentadien-1-yl derivative 4. On silica gel th...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1985-08-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9673 |
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| Summary: | Ozonolysis of α-terpineol (1) followed by steam distillation in the presence of acid is known to give 4-isopropylidenecyclopentenyl methyl ketone (3). In the absence of light, the latter is oxidized by air to the 4-(1-hydroperoxy-1-methylethyl)-1,3-cyclopentadien-1-yl derivative 4. On silica gel this compound formed two possible dimers (5, 6) of 3-acetyl-6,6-dimethylfulvene epoxide, the structures of which were established by X-ray crystallography. This work establishes by analogy, the stereochemistry of dimethylfulvene epoxide dimers previously described.
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| ISSN: | 0009-4293 2673-2424 |