Unusual reactions between chloroketenes and 1,3,5-tri-tert-butylcyclopentadiene
β Scribed by Dehmlow, Eckehard Volker ;Bollmann, Christof ;Neumann, Beate ;Stammler, Hans-Georg
- Book ID
- 102904221
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 554 KB
- Volume
- 1995
- Category
- Article
- ISSN
- 0947-3440
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β¦ Synopsis
Abstract
Reaction of title compound 1 with dichloroketene resulted in a complex rearrangement to 2 when the ketene was generated from Cl~3~CCOCl/Zn. In contrast, treatment of 1 with the ketene produced from dichloroacetyl chloride/triethylamine gave a bicyclo[3.2.0]heptenone (3) along with acylation product 4. Reaction of monochloroketene with 1 afforded the βnormalβοΈ endoβchloro compound 6 which thermally rearranged to the formal DielsβAlder product 7.
π SIMILAR VOLUMES
Title compound 1 is sterically shielded to such an extent that many "normal" reactions cannot occur. It is possible, however, to prepare the carboxylic acid 2, its acyl chloride 3 and the oxidation product 4. Furthermore, halogen substitutions to yield 5 and 6 and trialkylstannations to give 8a, b c
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