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Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene
✍ Scribed by Ian J.S Fairlamb; Julia M Dickinson; Ileana M Cristea
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 137 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladiumcatalysed [ π 2a+ π 2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions.
📜 SIMILAR VOLUMES
2+2)and (4+2)-cycloadducts are formed by thermal reaction of xanthenethione with allenes. Activation parameters for this "concerted two step" (a2s+s2s+n2S) reaction are presented. Photochemical addition of thiones to allenes have well been studied'. However, thermal addi-